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PubMed1992

Determination of hydroxychloroquine and its major metabolites in plasma using sequential achiral-chiral high-performance liquid chromatography.

A sequential achiral-chiral high-performance liquid chromatographic system has been developed for the determination of the enantiomers of hydroxychloroquine, (+)-HCQ and (-)-HCQ, and the enantiomers of its three major metabolites, bisdesethylchloroquine, desethylhydroxychloroquine and desethylchloroquine, in plasma. The HCQ was separated from the metabolites and interfering components in the plasma and quantified on a cyano-bonded phase, and the enantiomeric composition determined using a Chiral-AGP chiral stationary phase. The assay was validated and applied to the analysis of a pilot study of the pharmacokinetics of (+)- and (-)-HCQ in rabbits.

Animals↗
PubMed1992

Analytical and semi-preparative high-performance liquid chromatographic separation and assay of hydroxychloroquine enantiomers.

(+/-)-Hydroxychloroquine (HCQ) is an antimalarial and anti-arthritic drug which is administered as the racemate. An accurate, precise and sensitive high-performance liquid chromatographic assay was developed for the determination of HCQ enantiomers in samples from human plasma, serum, whole blood, and urine. After addition of (+/-)-chloroquine (internal standard), samples of blood component (0.5 ml) or urine (0.1 ml) were alkalinized and extracted with 5 ml of diethyl ether. After solvent evaporation the residues were derivatized with (+)-di-O-acetyl-L-tartaric anhydride at 45 degrees C for 30 min. The resulting diastereomers were then resolved using a C8 analytical column with a mobile phase consisting of 0.05 M KH2PO4 (pH 3)-methanol-ethanol-triethylamine (78:22:1:0.08). The ultraviolet detection wavelength was set at 343 nm. The derivatized HCQ enantiomers eluted in less than 40 min, free of interfering peaks. Excellent linear relationships (r2 > 0.997) were obtained between the area ratios and the corresponding plasma concentrations over a range of 12.5-500 ng/ml. The diastereomers could be hydrolysed using microwave energy and neutral pH, which enabled us to resolve the enantiomers on a semi-preparative (C18 column) scale. The method was suitable for the analysis and semi-preparative separation of HCQ enantiomers.

Adult↗
PubMed1995

Simple and specific reversed-phase liquid chromatographic method with diode-array detection for simultaneous determination of serum hydroxychloroquine, chloroquine and some corticosteroids.

This paper describes a simple, specific, and sensitive high-performance liquid chromatographic (HPLC) method using ion-pair reversed-phase chromatography with photodiode-array detection for the simultaneous determination of hydroxychloroquine (HCQ) and chloroquine (CQ) in serum samples from rheumatoid arthritis patients receiving either HCQ sulphate or CQ diphosphate. The assay is also applicable to the simultaneous determination of corticosteroids. The method consisted of two diethyl ether extractions of 1.0 ml of serum, to which two internal standards (2,3-diaminonaphthalene and 18-hydroxy-11-deoxycorticosterone) and 1.0 ml of 0.25 M sodium hydroxide had been added. After the organic phase was evaporated to dryness at 30-40 degrees C under a stream of nitrogen, the extract was reconstituted with a 1:1 mixture of 0.1 M perchloric acid and methanol, an aliquot of which was injected on to the system. Peak-height ratios at different wavelengths (A245/343, A245/256, A245/265 and A245/275) were utilized as a method of assessing peak homogeneity. Some anti-inflammatory drugs which may be used for rheumatic disorders were shown not to interfere with the assay. The method provides selectivity by using diode-array detection at several wavelengths. The use of two internal standards not only compensates for losses during the sample manipulation but also prevents erroneous results in case of interference.

Adrenal Cortex Hormones↗
PubMed2004

Safety of hydroxychloroquine in pregnant patients with connective tissue diseases. Review of the literature.

Hydroxychloroquine (HCQ) is widely used in the treatment of systemic lupus erythematosus (SLE). Even if it is generally agreed that pregnancy per se increases disease activity in patients with SLE and that withdrawal of HCQ at the onset of pregnancy may result in exacerbation of SLE, use of HCQ during pregnancy has remained controversial for a long time. Parke was the first to propose continuation of HCQ throughout gestation. Currently, more than 250 pregnancies resulting in live births have been reported and no increase in the rate of birth defects have been demonstrated. When studied, no retinal toxicity and ototoxicity have been found. Data concerning lactation and HCQ treatment are rare. However, the amount of HCQ received by children through lactation seems very low. In conclusion, HCQ should probably be maintained throughout pregnancy in patients with SLE and it does not seem necessary to advise against breastfeeding.

Antirheumatic Agents↗
PubMed2003

Hydroxychloroquine for the prevention of acute graft-versus-host disease after unrelated donor transplantation.

Hydroxychloroquine (HCQ) is an immunosuppressive agent that interferes with antigen presentation and with activity against graft-versus-host disease (GVHD). In a phase II trial assessing the GVHD prophylactic effects of HCQ, 51 consecutive unrelated donor transplant recipients received HCQ in addition to cyclosporin A, methylprednisolone, and methotrexate. HCQ was initiated on pretransplantation day -21 at 800 mg/d and continued until day +100 after transplantation. HCQ was extremely well tolerated and was not associated with side effects. Pharmacokinetic analyses demonstrated large inter- and intrapatient variability. The addition of HCQ did not affect posttransplantation immune recovery. Grade II to IV acute GVHD was observed in 56% of patients, and grade III and IV GVHD was observed in 17%. Day +100 mortality was 22%. When compared with a matched cohort of patients reported to the International Bone Marrow Transplant Registry, patients receiving HCQ had comparable cumulative incidences of grade II to IV acute GVHD. However, lower incidences of grades III and IV GVHD and better GVHD-free survival were observed in HCQ-treated patients (P =.01). We conclude that prophylactic HCQ is well tolerated and associated with a low incidence of severe acute GVHD. An ongoing placebo-controlled randomized trial will further determine what role HCQ plays in preventing GVHD after allografting.

Adolescent↗
PubMed2005

Enantioselective analysis of the metabolites of hydroxychloroquine and application to an in vitro metabolic study.

A one-step chiral method for the quantification of the enantiomers of two hydroxychloroquine (HCQ) metabolites, desethylchloroquine (DCQ) and desethylhydroxychloroquine (DHCQ) by HPLC is described, in addition to its application to the in vitro study of HCQ metabolism in rat liver microsomes. Liquid-liquid extraction was used to extract the enantiomers from microsome samples and the separation was performed on a Chiralpak AD-RH column protected with an RP-8 guard column using hexane:isopropanol (92:8, v/v) plus 0.1% diethylamine as the mobile phase, at a flow rate of 1.0 mL min(-1). The detection was carried out at 343 nm. The method proved to be linear in the range of 50-5000 ng mL(-1) for DCQ enantiomers and 125-2500ngmL(-1) for DHCQ enantiomers, with a quantification limit of 50 and 125 ng mL(-1), respectively. Precision and accuracy, demonstrated by within-day and between-day assays, were lower than 15%. The metabolic study demonstrated that metabolism is stereoselective for HCQ. The major metabolites formed in the incubation of racemic HCQ were (-)-(R)-DCQ and (-)-(R)-DHCQ with R/S ratios of 2.2 and 3.3, respectively.

Animals↗
PubMed2005

[Pleading to maintain hydroxychloroquine throughout Lupus pregnancies].

PURPOSE: The use of Hydroxychloroquine (HCQ) during pregnancy has remained controversial for a long time. However, it is generally agreed that pregnancy per se increases disease activity in patients with systemic lupus erythematosus (SLE) and that withdrawal of HCQ at the onset of pregnancy may result in exacerbation of SLE. Therefore, stopping HCQ at the onset of pregnancy may result in exacerbation of SLE which could be detrimental to both mother and fetus. CURRENT KNOWLEDGE AND KEY POINTS: The available data suggest that HCQ can be continued safely throughout pregnancy. After the first report by Parke of successful continuation of HCQ throughout gestation, more than 250 pregnancies resulting in live births have been reported and no increase in the rate of birth defects have been demonstrated. When studied, no retinal toxicity and ototoxicity have been found in the children. Data concerning lactation and HCQ treatment are rare. However, the amount of HCQ received by children through lactation seems very low. FUTURE PROSPECTS AND PROJECTS: For patients with SLE already taking HCQ, the benefits of continuing treatment with this medication throughout pregnancy seem to outweigh the hypothetical risks associated with its use. HCQ should probably be maintained throughout pregnancy in these patients with SLE and it does not seem necessary to advise against breastfeeding. Further studies with prospective follow-up of children exposed in utero to HCQ remain however needed to provide a definitive answer.

Antirheumatic Agents↗
PubMed2004

Hydroxychloroquine cardiotoxicity in systemic lupus erythematosus: a report of 2 cases and review of the literature.

BACKGROUND: Hydroxychloroquine (HCQ) is extensively used in the long-term treatment of systemic lupus erythematosus (SLE). Although considered by clinicians to be relatively safe, serious side effects have been documented in the literature. Retinotoxicity has received the most attention, whereas neuromyotoxicity and cardiotoxicity have been described in isolated case reports. We present 2 cases of potential cardiotoxicity occurring in patients with SLE while receiving long-term HCQ therapy. OBJECTIVE: To review the incidence, presentation, and mechanism of serious antimalarial toxicity, and to discuss the impact of HCQ on cardiac health in SLE. METHODS: The authors reviewed the English-language literature from 1948 to December 2002 using Medline databases. RESULTS: In addition to our patients, there are 2 published cases of biopsy-proven HCQ cardiotoxicity in the English-language literature. Both occurred in patients with SLE. The literature indicates that antimalarial cardiotoxicity may be of particular importance in patients with SLE given their already increased cardiac risk due to primary heart disease and accelerated atherosclerosis. Endomyocardial biopsy reveals a constellation of findings including vacuolar myopathy, myeloid bodies, and curvilinear bodies. CONCLUSIONS: As HCQ use among SLE patients increases, clinicians should be alert to the possibility of antimalarial cardiotoxicity. The potential severity and reversibility of this complication underscore the importance of timely diagnosis. The cases presented here, one with biopsy and one without, illustrate the utility of endomyocardial biopsy in HCQ-treated SLE patients with cardiac complaints to ensure accurate diagnosis and appropriate management.

Adult↗
PubMed2001

Analysis of the ABCR (ABCA4) gene in 4-aminoquinoline retinopathy: is retinal toxicity by chloroquine and hydroxychloroquine related to Stargardt disease?

PURPOSE: To determine if mutations in ABCR (ABCA4) are associated with chloroquine/hydroxychloroquine retinopathy. METHODS: DNA from eight patients with chloroquine or hydroxychloroquine retinopathy was studied. Controls were 80 individuals over age 65 years with normal retinal examinations. Ophthalmoscopy, color vision testing, visual fields, retinal photography, and fluorescein angiography were performed on the eight patients. Direct DNA sequencing of the exons and flanking intronic regions of the ABCR gene was completed for all patients. RESULTS: Clinical evaluation confirmed the diagnosis of chloroquine/hydroxychloroquine retinopathy and excluded Stargardt disease in each patient. Two patients had heterozygous ABCR missense mutations previously associated with Stargardt disease. None of the controls had these missense mutations. Three other patients had other missense polymorphisms. CONCLUSIONS: Some individuals who have ABCR mutations may be predisposed to develop retinal toxicity when exposed to chloroquine/hydroxychloroquine. We urge further study of a larger cohort of patients with chloroquine/hydroxychloroquine retinopathy.

ATP-Binding Cassette Transporters↗
PubMed1999

Inhibition of insulin metabolism by hydroxychloroquine and its enantiomers in cytosolic fraction of liver homogenates from healthy and diabetic rats.

To elucidate the mechanism by which hydroxychloroquine (HCQ) affects glucose metabolism, the effect of this drug and its enantiomers on insulin metabolism was studied using the cytosolic fraction of liver homogenates from healthy and diabetic rats. Eadie-Hofstee plots were monophasic suggesting that only a one-component enzyme system is involved in insulin degradation in the fraction used. Reaction velocity (V) vs substrate concentration plots were consistent with a Vmax model. HCQ caused a significant reduction in Vmax and Vmax/Km values in both healthy (Vmax, 3.63 +/- 0.46 vs 1.97 +/- 0.13, ng/min/mg; protein P < 0.001; and Vmax/Km 0.265 +/- 0.015 vs 0.112 +/- 0.004, ml/min/g protein) and diabetic rats (Vmax, 0.718 +/- 0.06 vs 0.360 +/- 0.024, ng/min/mg protein; and Vmax/Km, 0.05 +/- 0.002 vs 0.023 +/- 0.001, ml/min/g protein). Significant reduction in the V was observed in the presence of racemic (rac)-, R-, or S-HCQ. Ranking of the inhibitory potency was HCQ > S = R except at highest examined concentration (20 mg/mL) which was HCQ > S > R. In conclusion, the effect of HCQ on insulin degradation appears to be, in part, through inhibition of cytosolic insulin metabolizing enzyme. The effect is not stereoselective except at high concentrations. The R- and S-HCQ may have synergistic effects on inhibition of insulin degradation.

Animals↗
PubMed1998

Hydroxychloroquine improves airflow and lowers circulating IgE levels in subjects with moderate symptomatic asthma.

BACKGROUND: Although antiinflammatory therapy is accepted as the cornerstone of asthma treatment, available systemic immunosuppressive agents are not widely used because of justified concerns over potential toxicity. Hydroxychloroquine (HCQ) is a well-tolerated, safe immunomodulating drug, with proven efficacy in rheumatic diseases and known actions that suggest potential utility in the treatment of asthma. OBJECTIVE: We sought to assess the effectiveness of HCQ in subjects with moderate symptomatic asthma. METHODS: Symptomatic asthmatic subjects receiving stable doses of at least 6 puffs of inhaled corticosteroid per day with daily need for beta2-adrenergic agonists were studied. After baseline run-in, these subjects were randomized to 30 weeks of HCQ (n = 8) or placebo (n = 9). Objective measures included change from baseline mean FEV1, morning and evening peak flows, beta2-agonist use, IgE level, and need for rescue corticosteroids. Subjective symptom scores from bidaily diaries were also obtained. RESULTS: In the treatment group, mean FEV1 at the last 2 visits on therapy increased by 10.8% (P < .05), morning peak flows rose 16.2% (P < .03), evening peak flows rose 14.2% (P < .04), and beta2-agonist use fell 18.6% (P < .03). Mean IgE level declined 48% from 240 to 125 IU/mL. (P < .05). In the placebo group no significant change in these parameters occurred. Comparison of changes in these objective measures between the treatment and placebo groups failed to reach significance in the small population studied. Corticosteroid rescue interventions were required in 4 patients receiving placebo and 2 receiving HCQ. HCQ was well tolerated without notable side effects. CONCLUSIONS: Although the size of our sample population precludes definitive conclusions, these findings extend previous open-label observations. The late improvement in the HCQ group is consistent with its known slow onset of action. Further studies are warranted to confirm the antiasthmatic and antiallergic effects of HCQ and to investigate its potential as a disease-modifying agent.

Adolescent↗
PubMed2002

Hydroxychloroquine, hydroxycarbamide, and didanosine as economic treatment for HIV-1.

Most people who have HIV-1 and live in less-developed countries cannot afford standard combination antiretroviral therapy, and more economical approaches to treatment are therefore needed. We treated 22 patients who were infected with HIV-1 (viral load < 100000 copies/mL and CD4 count >150 cells/microL) with hydroxychloroquine (200 mg), hydroxycarbamide (hydroxyurea) (500 mg), and didanosine (125-200 mg), taken twice daily. Treatment was well tolerated, with few serious adverse events. Viral load showed a sustained decrease of 1 3 log, and CD4 count was maintained (percentage increase; 2 9%) over 48 weeks in the 16 evaluable patients. This new combination of drugs could be suitable for countries that have restricted resources, but should first be further investigated.

Adult↗
PubMedDate not supplied

Inhibition of HIV-1 replication by hydroxychloroquine: mechanism of action and comparison with zidovudine.

We have previously described the inhibition of human immunodeficiency virus serotype 1 (HIV-1) using the antimalarial hydroxychloroquine (HCQ), a weak base that inhibits the posttranslational modification of glycoprotein 120 (gp 120) in T cells and monocytes. The mechanism of inhibition of gp 120 production was presumed to be the ability of HCQ to increase endosomal pH and therefore alter enzymes required for gp120 production. To further clarify this action, we have determined the effect of HCQ and its enantiomers on endosomal pH. Pretreatment of cells with HCQ and the levo- and dextro-enantiomers at concentrations demonstrated to suppress anti-HIV-1 activity increased endosomal pH to levels similar to increases seen with chloroquine and ammonium chloride, two other weak bases, and decreased gp 120 production. The dextro- and levo-enantiomers suppressed HIV-1 replication to a similar extent and were no more toxic than racemic HCQ. We next compared the anti-HIV-1 effect of HCQ with zidovudine (ZDV) in both newly and chronically HIV-1-infected T-cell and monocytic cell lines (63 and 63HIV). HCQ suppressed HIV-1 replication in a dose-dependent manner in both recently and chronically infected T-cell and monocytic cell lines. In contrast, ZDV pretreatment had potent anti-HIV-1 activity in the newly infected T and monocytic cells but not in chronically infected cells. An additive effect of HCQ with ZDV was observed in the newly infected T and monocytic cells but not in the chronically infected cells. Although the anti-HIV-1 effect of HCQ was less than that of ZDV, HCQ may still be potentially useful either as an alternative HIV-1 treatment or in combination with other anti-HIV-1 agents, especially in patients who have rheumatic manifestations of HIV-1 infection.

Anti-HIV Agents↗
PubMedDate not supplied

Comparison of hydroxychloroquine with zidovudine in asymptomatic patients infected with human immunodeficiency virus type 1.

Hydroxychloroquine (HCQ), an antimalarial agent used to treat patients with autoimmune diseases, has been shown to suppress human immunodeficiency virus type 1 (HIV-1) replication in T cells and monocytes in vitro by inhibiting posttranscriptional modification of the virus. An initial randomized, placebo-controlled clinical trial conducted in 38 asymptomatic HIV-1-infected patients who had CD4+ counts between 200 and 500 cells/mm3 demonstrated that the amount of recoverable virus declined significantly in the HCQ group compared with the placebo group over the 8-week study period. These preliminary observations were expanded into a second 16-week clinical trial comparing the efficacy of HCQ with that of zidovudine (ZDV) in 72 asymptomatic HIV-1-infected patients with CD4+ counts between 200 and 500 cells/mm3. Patients were randomly assigned to receive either HCQ 800 mg/d (n = 35) or ZDV 500 mg/d (n = 37) for 16 weeks. No adverse reactions to the study medications were observed in either the HCQ or ZDV group. Patients in both groups had reduced levels of recoverable HIV-1 RNA in the plasma, reduced levels of cultured virus, and reduced levels of serum p24 antigen after the 16-week study period. However, no difference was noted in absolute CD4+ counts between the two groups. Interleukin-6 and serum immunoglobulin G levels were significantly reduced in the HCQ group but not in the ZDV group. These findings support the results of the previous clinical trial. Thus HCQ may be potentially useful in the treatment of patients with HIV-1 infection.

Adult↗
PubMed2003

The incidence of irreversible retinal toxicity in patients treated with hydroxychloroquine: a reappraisal.

PURPOSE: To define the risk of hydroxychloroquine (HCQ)-related retinal toxicity in patients with rheumatoid arthritis (RA) and systemic lupus erythematosus (SLE) who are receiving recommended dosages of the drug (< or =6.5 mg/kg/day). DESIGN: Prospective cohort study, from 1985 to 2000. PARTICIPANTS: Greek patients with RA (n = 335) and SLE (n = 191) treated with HCQ, 400 of whom had completed at least 6 years of treatment. METHODS: Ophthalmologic evaluation was performed every 6 months from 1985 to 1995, and yearly thereafter. This consisted of best-corrected visual acuity, color vision testing, static central visual field testing, fundoscopy, electroretinography, and fluorescein angiography, when indicated. MAIN OUTCOME MEASURES: Fundus lesions attributed to HCQ. RESULTS: No HCQ retinal toxicity was noted in any of the 526 patients during the first 6 years of treatment. Two (3.4%) of the first 58 long-term (>6 years) treated patients developed HCQ-related maculopathy at 8 and 6.5 years of treatment, despite regular ophthalmologic evaluation. On follow-up 7 and 9 years after cessation of HCQ treatment, both patients had stable eye disease. No HCQ retinal toxicity was observed in the subsequent 342 patients who were treated for >6 years. Overall, the incidence of HCQ-related retinopathy in 400 patients who were treated with recommended dosages of the drug for a mean of 8.7 years was reduced to 0.5%. CONCLUSIONS: After a baseline ophthalmic examination to confirm the absence of preexisting fundus pathology, patients with normal renal function may receive HCQ at a maximal daily dosage of 6.5 mg/kg and continue safely for 6 years. However, annual screening is recommended in patients who have taken the drug, even in recommended doses, for >6 years.

Adolescent↗
PubMed2002

The effectiveness of hydroxychloroquine in patients with type 2 diabetes mellitus who are refractory to sulfonylureas--a randomized trial.

AIM: To assess the glucose-lowering efficacy, responsiveness, duration of action and impact on quality-of-life of hydroxychloroquine (HXCHL), when added as an antihyperglycemic agent to patients with sulfonylurea-refractory type 2 diabetes. METHODS: One hundred and thirty-five obese patients with type 2 diabetes (mean age 57.5 years) and a glycated hemoglobin (GHb) > or = 11% despite maximum sulfonylureas were randomly allocated to the addition of HXCHL (up to 300 mg bid) or placebo and followed for up to 18 months. Randomization was stratified by baseline GHb (<13.5% versus > or = 13.5%). The primary outcome was 'blinded' withdrawal of study drug due to unacceptable glycemic control; GHb, glucose tolerance, lipids, and quality of life were also assessed. RESULTS: Those on placebo were more likely to be withdrawn from study drug because of unacceptable glycemic control than patients randomized to HXCHL (95.5 and 69.6% given placebo and HXCHL, respectively; P=0.0001). During the first 6 months, HXCHL decreased GHb by an absolute amount of 1.02% more than placebo (95% CI 0.24, 1.81). Glucose tolerance and LDL cholesterol improved during the first 3 months of therapy. No significant adverse effects were noted. Factors that predicted responsiveness included an initial GHb <13.5%, early responsiveness to study drug, and no prior metformin use. Lower GHb levels at baseline predicted a better response; the hazard of withdrawal increased 36% (95% CI 11%, 66%) for every 1% increase in GHb even in patients whose baseline GHb was <13.5%. CONCLUSIONS: HXCHL improves glycemic control in sulfonylurea-refractory patients with poorly controlled type 2 diabetes.

Body Mass Index↗
PubMed2004

[Analysis of 925 patients on long-term hydroxychloroquine or chloroquine treatment: results of ophthalmological screening].

PURPOSE: The aim of this 4-Year study was to analyze the population referred to our laboratory for the visual follow-up of hydroxychloroquine or chloroquine treatment. MATERIAL AND METHODS: We received 925 patients: 78% female, 22% male. For each patient, a 13-item criteria was filled out and regular exams were performed. The pathologies were divided in to 4 groups: rheumatoid polyarthritis (P), lupus (L), sarcoidosis (S), others (O). RESULTS: The pathologies were distributed as follows: 48% "P", 29% "L", 3% "S", 1% "P + L", 19% "O". Of these patients, 19% had less than 1 Year of treatment, 73% 1-10 Years and 8% more than 10 Years. The screening exposed no retinal intoxications but 3% presented pre-clinical intoxication (PCI) and 80% were allowed to continue their treatment. The most important statistical results were: 1) a significant relation between the PCI and the duration of the treatment (p<0.001); 2) a non-significant relation between the PCI and the daily dose (p=0.417); and 3) a significant relation between PCI and the cumulative dose (p=0.003). CONCLUSION: The results shows the advantage of the ERG in screening to prevent anti-malarial retinal toxicity. This study confirms that the cumulative dose seems to be more important than the daily dose, but we agree with the international consensus to respect a daily dose under 6.5 mg/kg/d. The results also demonstrated that, with this large and diversified population, there is a need for prospective and multi-centric studies. With the above results, international standards should be established in order to obtain the most efficient screening for each category of patient.

Antirheumatic Agents↗
PubMed1983

Treatment of cutaneous pseudolymphoma with hydroxychloroquine.

A 45-year-old woman with generalized cutaneous pseudolymphoma of Spiegler-Fendt was successfully treated with hydroxychloroquine. It is felt that the suppression of lymphocyte and/or histiocyte function was responsible for the remission of the disease. This is apparently the first report of cutaneous pseudolymphoma of Spiegler-Fendt being successfully treated with antimalarials. The differentiation between cutaneous pseudolymphoma and cutaneous malignant lymphoma is also discussed.

Diagnosis, Differential↗