Isotretinoin

Identification

Summary

Isotretinoin is a retinoid used to treat severe recalcitrant acne.

Brand Names

Absorica, Accutane, Amnesteem, Claravis, Clarus, Epuris, Myorisan, Sotret, Zenatane

Generic Name

Isotretinoin

DrugBank Accession Number

DB00982

Background

Isotretinoin is a retinoid derivative of vitamin A used in the treatment of severe recalcitrant acne.^Label It was most widely marketed under the brand name Accutane, which has since been discontinued.¹⁰ Isotretinoin is associated with major risks in pregnancy and is therefore only available under the iPLEDGE program in the United States.¹² The first isotretinoin-containing product was FDA approved on 7 May 1982.¹⁰

Type

Small Molecule

Groups

Approved

Structure

Similar Structures

Weight: Average: 300.4351
Monoisotopic: 300.20893014
Chemical Formula: C₂₀H₂₈O₂

Synonyms

(7E,9E,11E,13Z)-retinoic acid
13-cis-retinoic acid
13-cis-Vitamin A acid
13-RA
cis-RA
Isotretinoin
Isotretinoína
Isotrétinoine
Isotretinoino
Isotretinoinum
Neovitamin A acid

External IDs

RO 4-3780
RO-4-3780

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Pharmacology

Indication

Isotretinoin is indicated to treat severe recalcitrant nodular acne and patients ≥12 years enrolled in the iPLEDGE program.^Label,12

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Associated Conditions

Indication Type	Indication	Approval Level	Dose Form
Treatment of	Acne conglobata	••••••••••••	•••••••
Treatment of	Neuroblastoma	••• •••••
Treatment of	Rosacea	••• •••••
Treatment of	Sezary syndrome	••• •••••
Treatment of	Early mycosis fungoides (mf)	••• •••••

Contraindications & Blackbox Warnings

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Pharmacodynamics

The pharmacodynamics of isotretinoin are poorly understood.^Label

Mechanism of action

Isotretinoin produces its effects through altering progress through the cell cycle, cell differentiation, survival, and apoptosis.⁴ These actions reduce sebum production, preventing the blockage of pores, and growth of acne causing bacteria.⁴ Isotretinoin and 4-oxo-isotretinoin both significantly reduce the production of sebum.^4,Label Isotretinoin has little to no affinity for retinol binding proteins (RBPs) and retinoic acid nuclear receptors (RARs).⁴ Tretinoin and 4-oxo-tretinion bind to the RAR-γ receptor, which is suspected to be part of the action of acne treatment by isotretinoin.⁴ Isotretinoin induces apoptosis in sebocytes, leading to a decrease in sebum production.⁴ Isotretinoin also reduces the formation of comedones by reducing hyperkeratinization through an unknown mechanism.⁴ Isotretinoin does not directly kill bacteria but it does reduce the size of sebum ducts and makes the microenvironment less hospitable to acne causing bacteria.⁴ It may also increase immune mechanisms and alter chemotaxis of monocytes to reduce inflammation.⁴

There is preliminary evidence suggesting isotretinoin may interact with FoxO1, which may explain a substantial number of isotretinoin's unexplained actions.⁹

Target	Actions	Organism
URetinoic acid receptor gamma	Not Available	Humans
URetinoic acid receptor alpha	other/unknown	Humans

Absorption

Patients reach a maximum concentration of 74-511ng/mL after 1-4 hours following a 100mg oral dose.¹ Isotretinoin is better absorbed with a high fat meal and bioavailability may change from one brand to another.^Label

Following a 40mg oral dose, fasted subjects reached a maximum concentration of 314ng/mL in 2.9 hours with an area under the curve of 4055ng/mL*hr.^Label Subjects given a high fat meal and a 40mg oral doses reached a maximum concentration of 395ng/mL in 6.4 hours with an area under the curve of 6095ng/mL*mL.^Label

Volume of distribution

The volume of distribution in humans is unknown because there is no intravenous preparation.¹³ In a study of pediatric patients with neuroblastoma the volume of distribution was found to be 85L.⁶ The volume of distribution was also found to be 2432mL/kg in guinea pigs and 1716mL/kg in obese rats.⁵

Protein binding

Isotretinoin is >99.9% protein bound, mainly to serum albumin.^Label

Metabolism

Isotretinoin, or 13-cis-retinoic acid can undergo reversible cis-trans isomerization to all-trans-retinoic acid.⁸ Isotretinoin undergoes 4-hydroxylation to 4-hydroxy-13-cis-retinoic acid, which is oxidized to the main metabolite 4-oxo-13-cis-retinoic acid.^8,3. All-trans-retinoic acid undergoes 4-hydroxylation to 4-hydroxy-all-trans-retinoic acid, which is oxidized to 4-oxo-all-trans-retinoic acid.⁸ 4-oxo-13-cis-retinoic acid can undergo reversible cis-trans isomerization to 4-oxo-all-trans-retinoic acid.⁸

Hover over products below to view reaction partners

Isotretinoin
- all-trans-retinoic acid
  - 4-hydroxy-all-trans-retinoic acid
    - 4-oxo-all-trans-retinoic acid
      - 4-oxo-13-cis-retinoic acid
- 4-hydroxy-13-cis-retinoic acid
  - 4-oxo-13-cis-retinoic acid
    - 4-oxo-all-trans-retinoic acid

Route of elimination

Isotretinoin and its metabolites are conjugated and excreted in the urine and feces in similar amounts.^Label 53-74% of an oral dose is eliminated as unchanged isotretinoin in the feces.¹

Half-life

The half life ranges from 7-39 hours¹³ with a mean elimination half life of 20 hours.¹ The half life of 4-oxo-13-cis-retinoic acid ranges from 17-50 hours with a mean elimination half life of 25 hours.¹³

Clearance

The clearance of isotretinoin is 15.9L/h in pediatric patients with neuroblastoma.⁶ Clearance is also 21.3mL/min/kg in guinea pigs and 7.2mL/min/kg in obese rats.⁵

Adverse Effects

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Toxicity

Patients experiencing an overdose may present with vomiting, facial flushing, cheilosis, abdominal pain, headache, dizziness, and ataxia.^Label These symptoms may rapidly resolve.^Label Generally no treatment is required for these overdoses.⁷

The oral lowest dose causing toxic effect (TDLO) for children is 30mg/kg/21W, oral TDLO for men is 24mg/kg/4W, oral TDLO for women is 56mg/kg/8W.¹⁴ The intraperitoneal LD₅₀ for rats is 901mg/kg, oral LD₅₀ for mice is 3389mg/kg, oral LD₅₀ for rats is >4000mg/kg.¹⁴

Isotretinoin is associated with major congenital malformations, spontaneous abortion, and premature birth.^Label It is unknown if isotretinoin is expressed in breast milk but due to the associated hazards a decision should be made to either stop nursing or stop taking isotretinoin.^Label

In animal studies, isotretinoin was associated with an increased risk of pheochromocytoma and adrenal medullary hyperplasia at doses above the recommended clinical dose.^Label Isotretinoin was negative for the Ames test of mutagenicity once and weakly positive a second time.^Label It has not been shown to be clastogenic.^Label A study in dogs noted testicular atrophy after doses of 10-30 times the recommended clinical dose for 30 weeks.^Label In trials with men there were no effects seen on sperm count, motility, morphology, ejaculate volume, and seminal plasma fructose.^Label

Pathways

Not Available

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Not Available

Interactions

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This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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Abacavir	Isotretinoin may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abametapir	The serum concentration of Isotretinoin can be increased when it is combined with Abametapir.
Aceclofenac	Aceclofenac may decrease the excretion rate of Isotretinoin which could result in a higher serum level.
Acemetacin	Acemetacin may decrease the excretion rate of Isotretinoin which could result in a higher serum level.
Acetaminophen	Acetaminophen may decrease the excretion rate of Isotretinoin which could result in a higher serum level.

Food Interactions

Avoid alcohol. Alcohol with isotretinoin can lead to inflammation of the liver.
Avoid vitamin A supplements.
Take with food. High-fat food increases drug absorption.

Products

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Product Images

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Absorica	Capsule	20 mg/1	Oral	Sun Pharmaceutical Industries, Inc.	2012-06-08	Not applicable
Absorica	Capsule	40 mg/1	Oral	Sun Pharmaceutical Industries, Inc.	2012-06-08	Not applicable
Absorica	Capsule	10 mg/1	Oral	Sun Pharmaceutical Industries, Inc.	2012-06-08	Not applicable
Absorica	Capsule	35 mg/1	Oral	Sun Pharmaceutical Industries, Inc.	2015-02-17	Not applicable
Absorica	Capsule	30 mg/1	Oral	Sun Pharmaceutical Industries, Inc.	2012-06-08	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Accutane	Capsule, gelatin coated	40 mg/1	Oral	Jg Pharma Inc.	2022-08-01	Not applicable
Accutane	Capsule, gelatin coated	20 mg/1	Oral	Jg Pharma Inc.	2021-01-11	2023-11-30
Accutane	Capsule, gelatin coated	20 mg/1	Oral	Jg Pharma Inc.	2022-08-01	Not applicable
Accutane	Capsule, gelatin coated	30 mg/1	Oral	Jg Pharma Inc.	2021-01-11	2024-01-31
Accutane	Capsule, gelatin coated	10 mg/1	Oral	Jg Pharma Inc.	2021-01-11	2023-12-31

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
ETREXİN % 2 + % 0.05 JEL	Isotretinoin (0.05 %) + Erythromycin (2 %)	Gel	Topical	VEM İLAÇ SAN. VE TİC. A.Ş.	2014-04-07	Not applicable
ISOTREXIN JEL, 30 G	Isotretinoin (0.05 %) + Erythromycin (2 %)	Gel	Topical	GLAXOSMİTHKLİNE İLAÇLARI SAN. VE TİC. A.Ş.	2010-07-06	2020-05-28
MUNDERM JEL , 30 GRAM	Isotretinoin (0.5 mg) + Erythromycin (20 mg)	Gel	Topical	HELBA İLAÇ İÇ VE DIŞ SAN. TİC. A.Ş.	2014-11-14	Not applicable

Chemical Identifiers

UNII: EH28UP18IF
CAS number: 4759-48-2
InChI Key: SHGAZHPCJJPHSC-XFYACQKRSA-N
InChI: InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14-
IUPAC Name: (2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
SMILES: C\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C\C(O)=O

References

Synthesis Reference

Ashok Kumar, Dharmendra Singh, Ganesh Devidas Mahale, Ragnesh Kumar Rana, Mahesh Kharade, "PROCESS FOR PREPARATION OF HIGHLY PURE ISOTRETINOIN." U.S. Patent US20080207946, issued August 28, 2008.

US20080207946

General References

Khoo KC, Reik D, Colburn WA: Pharmacokinetics of isotretinoin following a single oral dose. J Clin Pharmacol. 1982 Aug-Sep;22(8-9):395-402. [Article]
Miastkowska M, Sikora E, Ogonowski J, Zielina M, Łudzik A: The kinetic study of isotretinoin release from nanoemulsion Colloids and Surfaces A: Physicochemical and Engineering Aspects. 2016 Dec 5;510:63-68. [Article]
Vane FM, Bugge CJ: Identification of 4-oxo-13-cis-retinoic acid as the major metabolite of 13-cis-retinoic acid in human blood. Drug Metab Dispos. 1981 Nov-Dec;9(6):515-20. [Article]
Layton A: The use of isotretinoin in acne. Dermatoendocrinol. 2009 May;1(3):162-9. doi: 10.4161/derm.1.3.9364. [Article]
Chien DS, Sandri RB, Tang-Liu DS: Systemic pharmacokinetics of acitretin, etretinate, isotretinoin, and acetylenic retinoids in guinea pigs and obese rats. Drug Metab Dispos. 1992 Mar-Apr;20(2):211-7. [Article]
Veal GJ, Cole M, Errington J, Pearson AD, Foot AB, Whyman G, Boddy AV: Pharmacokinetics and metabolism of 13-cis-retinoic acid (isotretinoin) in children with high-risk neuroblastoma - a study of the United Kingdom Children's Cancer Study Group. Br J Cancer. 2007 Feb 12;96(3):424-31. doi: 10.1038/sj.bjc.6603554. Epub 2007 Jan 16. [Article]
Aubin S, Lorette G, Muller C, Vaillant L: Massive isotretinoin intoxication. Clin Exp Dermatol. 1995 Jul;20(4):348-50. [Article]
Brazzell RK, Colburn WA: Pharmacokinetics of the retinoids isotretinoin and etretinate. A comparative review. J Am Acad Dermatol. 1982 Apr;6(4 Pt 2 Suppl):643-51. [Article]
Melnik BC: Isotretinoin and FoxO1: A scientific hypothesis. Dermatoendocrinol. 2011 Jul;3(3):141-65. doi: 10.4161/derm.3.3.15331. Epub 2011 Jul 1. [Article]
FDA Approved Drug Products: Accutane Oral Capsule [Link]
FDA Approved Drug Products: Absorica [Link]
iPLEDGE Program Home Page [Link]
New Zealand Drug Data Sheet: Oratane [Link]
Isotretinoin MSDS [Link]
Health Canada Product Monograph: Accutane Roche (isotretinoin) capsules for oral administration [Link]

External Links

Human Metabolome Database: HMDB0006219
KEGG Drug: D00348
PubChem Compound: 5282379
PubChem Substance: 46508729
ChemSpider: 4445539
BindingDB: 50031459
RxNav: 6064
ChEBI: 6067
ChEMBL: CHEMBL547
ZINC: ZINC000003792789
Therapeutic Targets Database: DAP000009
PharmGKB: PA450128
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
Wikipedia: Isotretinoin

FDA label

Download (175 KB)

MSDS

Download (37.3 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Diagnostic	Acne Vulgaris	1
4	Completed	Basic Science	Adverse Drug Reaction (ADR)	1
4	Completed	Diagnostic	Acne Vulgaris	1
4	Completed	Other	CYP2D6 Polymorphism	1
4	Completed	Prevention	Proliferative Vitreoretinopathy	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Barr Pharmaceuticals
Catalent Pharma Solutions
F Hoffmann-La Roche Ltd.
Mylan
Pharmaceutical Utilization Management Program VA Inc.
Physicians Total Care Inc.
Ranbaxy Laboratories

Dosage Forms

Form	Route	Strength
Capsule	Oral	25 mg/1
Capsule	Oral	35 mg/1
Capsule	Oral	16 mg
Capsule	Oral	16 mg/1
Capsule	Oral	24 mg
Capsule	Oral	24 mg/1
Capsule	Oral	28 mg/1
Capsule	Oral	32 mg/1
Capsule	Oral	32 mg
Capsule	Oral	8 mg
Capsule	Oral	8 mg/1
Capsule, liquid filled	Oral	10 mg/1
Capsule, liquid filled	Oral	40 mg/1
Capsule	Oral	40 mg
Capsule, gelatin coated	Oral	10 mg
Capsule, gelatin coated	Oral	20 mg
Capsule	Oral	10 mg/1
Capsule	Oral	20 mg/1
Capsule	Oral	40 mg/1
Capsule	Oral
Capsule	Oral	30 mg/1
Capsule, liquid filled	Oral	30 mg/1
Capsule, liquid filled	Oral	0.21 mg
Capsule	Oral	30 mg
Gel	Topical
Capsule	Oral	10.00 mg
Capsule, liquid filled	Oral	10 mg
Capsule, liquid filled	Oral	20 mg
Capsule, liquid filled	Oral	30 mg
Capsule, liquid filled	Oral	40 mg
Capsule, liquid filled	Oral	4000000 mg
Capsule, liquid filled	Oral	5 mg
Gel	Topical	50 mg
Gel	Topical	0.05 g
Capsule, liquid filled	Oral	1000000 mg
Capsule, liquid filled	Oral	2000000 mg
Cream	Topical
Gel	Topical	0.05 %
Gel	Topical
Capsule	Oral	20.0000 mg
Capsule	Oral	5.0000 mg
Capsule	Oral	20.00 mg
Capsule	Oral	5 MG
Capsule	Oral	20.000 mg
Capsule, gelatin coated	Oral	10 mg/1
Capsule, gelatin coated	Oral	30 mg/1
Capsule, gelatin coated	Oral	40 mg/1
Capsule, liquid filled	Oral	20 mg/1
Capsule	Oral	20 mg
Capsule	Oral	10.000 mg
Capsule	Oral	10.0000 mg
Capsule, gelatin coated	Oral	20 mg/1
Capsule	Oral	10 mg

Prices

Unit description	Cost	Unit
Accutane 20 mg capsule	23.77USD	capsule
Amnesteem 40 mg capsule	22.6USD	capsule
Claravis 40 mg capsule	22.6USD	capsule
Amnesteem 20 mg capsule	19.45USD	capsule
Claravis 20 mg capsule	18.7USD	capsule
Claravis 30 mg capsule	16.45USD	capsule
Amnesteem 10 mg capsule	16.4USD	capsule
Claravis 10 mg capsule	15.77USD	capsule
Accutane 40 mg capsule	14.88USD	capsule
Accutane 10 mg capsule	10.55USD	capsule
Sotret 40 mg capsule	10.08USD	capsule
Sotret 20 mg capsule	8.67USD	capsule
Sotret 30 mg capsule	8.44USD	capsule
Sotret 10 mg capsule	7.31USD	capsule
Clarus 40 mg Capsule	2.14USD	capsule
Clarus 10 mg Capsule	1.05USD	capsule

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US8367102	No	2013-02-05	2021-09-21
US9089534	No	2015-07-28	2021-09-21
US7435427	No	2008-10-14	2021-09-21
US9078925	No	2015-07-14	2021-09-21
US8952064	No	2015-02-10	2021-09-21
US9750711	No	2017-09-05	2035-05-29
US9700535	No	2017-07-11	2035-08-04

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	189-190	MSDS
boiling point (°C)	462.8	http://www.chemspider.com/Chemical-Structure.4445539.html
water solubility	0.00477mg/mL	https://www.sciencedirect.com/science/article/pii/S0927775716305817
logP	5.66	https://www.sciencedirect.com/science/article/pii/S0927775716305817
pKa	~4	https://www.rochecanada.com/content/dam/rochexx/roche-ca/products/ConsumerInformation/MonographsandPublicAdvisories/Accutane/Accutane_PM_E.pdf

Predicted Properties

Property	Value	Source
Water Solubility	0.00477 mg/mL	ALOGPS
logP	5.66	ALOGPS
logP	5.01	Chemaxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	4.76	Chemaxon
Physiological Charge	-1	Chemaxon
Hydrogen Acceptor Count	2	Chemaxon
Hydrogen Donor Count	1	Chemaxon
Polar Surface Area	37.3 Å²	Chemaxon
Rotatable Bond Count	5	Chemaxon
Refractivity	97.79 m³·mol^-1	Chemaxon
Polarizability	36.15 Å³	Chemaxon
Number of Rings	1	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	Yes	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9925
Blood Brain Barrier	+	0.9311
Caco-2 permeable	+	0.7603
P-glycoprotein substrate	Non-substrate	0.6144
P-glycoprotein inhibitor I	Non-inhibitor	0.8912
P-glycoprotein inhibitor II	Non-inhibitor	0.8088
Renal organic cation transporter	Non-inhibitor	0.8639
CYP450 2C9 substrate	Non-substrate	0.8221
CYP450 2D6 substrate	Non-substrate	0.9115
CYP450 3A4 substrate	Substrate	0.6025
CYP450 1A2 substrate	Non-inhibitor	0.9046
CYP450 2C9 inhibitor	Non-inhibitor	0.8831
CYP450 2D6 inhibitor	Non-inhibitor	0.9231
CYP450 2C19 inhibitor	Non-inhibitor	0.9025
CYP450 3A4 inhibitor	Non-inhibitor	0.9301
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9252
Ames test	Non AMES toxic	0.8944
Carcinogenicity	Non-carcinogens	0.7081
Biodegradation	Ready biodegradable	0.5554
Rat acute toxicity	2.1455 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9562
hERG inhibition (predictor II)	Non-inhibitor	0.9538

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-052r-2090000000-42b8aa0666b5a088671b
MS/MS Spectrum - Quattro_QQQ 10V, Positive	LC-MS/MS	splash10-0udi-0009000000-12dbd83959268dee6dbf
MS/MS Spectrum - Quattro_QQQ 25V, Positive	LC-MS/MS	splash10-066r-4900000000-31c9262cbbf0bad5b738
MS/MS Spectrum - Quattro_QQQ 40V, Positive	LC-MS/MS	splash10-0fsl-9600000000-c6681587f0a9ae7a712e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-001i-0390000000-af1a6974c2a7872f36c7
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a4i-0090000000-82a486e1feafa5cf4f1b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a4i-0190000000-08192331c8e265ce508b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-00lu-2970000000-05e8c3f4df3fed93b093
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-000i-2890000000-2b136364b4a3a972b85b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-052f-4910000000-f6c3b4ffdf3dc3f695a2
1H NMR Spectrum	1D NMR	Not Applicable
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable
[1H,13C] 2D NMR Spectrum	2D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	202.7295981	predicted	DarkChem Lite v0.1.0
[M-H]-	203.3218981	predicted	DarkChem Lite v0.1.0
[M-H]-	189.60449	predicted	DeepCCS 1.0 (2019)
[M+H]+	191.9625	predicted	DeepCCS 1.0 (2019)
[M+Na]+	199.03537	predicted	DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.

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Details1. Retinoic acid receptor gamma

Kind: Protein
Organism: Humans
Pharmacological action: Unknown

General Function: Zinc ion binding
Specific Function: Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expressi...
Gene Name: RARG
Uniprot ID: P13631
Uniprot Name: Retinoic acid receptor gamma
Molecular Weight: 50341.405 Da

References

Layton A: The use of isotretinoin in acne. Dermatoendocrinol. 2009 May;1(3):162-9. doi: 10.4161/derm.1.3.9364. [Article]

Details2. Retinoic acid receptor alpha

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Other/unknown

General Function: Zinc ion binding
Specific Function: Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expressi...
Gene Name: RARA
Uniprot ID: P10276
Uniprot Name: Retinoic acid receptor alpha
Molecular Weight: 50770.805 Da

References

Dahl AR, Grossi IM, Houchens DP, Scovell LJ, Placke ME, Imondi AR, Stoner GD, De Luca LM, Wang D, Mulshine JL: Inhaled isotretinoin (13-cis retinoic acid) is an effective lung cancer chemopreventive agent in A/J mice at low doses: a pilot study. Clin Cancer Res. 2000 Aug;6(8):3015-24. [Article]
Zouboulis CC: Isotretinoin revisited: pluripotent effects on human sebaceous gland cells. J Invest Dermatol. 2006 Oct;126(10):2154-6. [Article]
Vu-Dac N, Gervois P, Torra IP, Fruchart JC, Kosykh V, Kooistra T, Princen HM, Dallongeville J, Staels B: Retinoids increase human apo C-III expression at the transcriptional level via the retinoid X receptor. Contribution to the hypertriglyceridemic action of retinoids. J Clin Invest. 1998 Aug 1;102(3):625-32. [Article]
Taylor LE, Bennett GD, Finnell RH: Altered gene expression in murine branchial arches following in utero exposure to retinoic acid. J Craniofac Genet Dev Biol. 1995 Jan-Mar;15(1):13-25. [Article]
Shroot B, Michel S: Pharmacology and chemistry of adapalene. J Am Acad Dermatol. 1997 Jun;36(6 Pt 2):S96-103. [Article]

Enzymes

Details1. Cytochrome P450 3A4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Vitamin d3 25-hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name: CYP3A4
Uniprot ID: P08684
Uniprot Name: Cytochrome P450 3A4
Molecular Weight: 57342.67 Da

References

Hendrix CW, Jackson KA, Whitmore E, Guidos A, Kretzer R, Liss CM, Shah LP, Khoo KC, McLane J, Trapnell CB: The effect of isotretinoin on the pharmacokinetics and pharmacodynamics of ethinyl estradiol and norethindrone. Clin Pharmacol Ther. 2004 May;75(5):464-75. doi: 10.1016/j.clpt.2004.01.003. [Article]

Carriers

Details1. Serum albumin

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Binder

General Function: Toxic substance binding
Specific Function: Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name: ALB
Uniprot ID: P02768
Uniprot Name: Serum albumin
Molecular Weight: 69365.94 Da

References

Layton A: The use of isotretinoin in acne. Dermatoendocrinol. 2009 May;1(3):162-9. doi: 10.4161/derm.1.3.9364. [Article]
Tsukada M, Schroder M, Seltmann H, Orfanos CE, Zouboulis CC: High albumin levels restrict the kinetics of 13-cis retinoic acid uptake and intracellular isomerization to all-trans retinoic acid and inhibit its anti-proliferative effect on SZ95 sebocytes. J Invest Dermatol. 2002 Jul;119(1):182-5. doi: 10.1046/j.1523-1747.2002.01816.x. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55

Isotretinoin

Identification

Structure for Isotretinoin (DB00982)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References

References

Enzymes

References

Carriers

References