Isotretinoin | Dermatologic agent | CAS# 4759-48-2

MedKoo Cat#: 571398 | Name: Isotretinoin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Isotretinoin is a topical dermatologic agent that is used in the treatment of acne and several other skin diseases. It may also treat depression and anxiety. The drug has teratogenic and other adverse effects.

Chemical Structure

Isotretinoin

CAS#4759-48-2

Theoretical Analysis

MedKoo Cat#: 571398

Name: Isotretinoin

CAS#: 4759-48-2

Chemical Formula: C20H28O2

Exact Mass: 300.2089

Molecular Weight: 300.44

Elemental Analysis: C, 79.96; H, 9.39; O, 10.65

Price and Availability

Size	Price	Availability
500mg	USD 90.00	Ready to ship
1g	USD 150.00	Ready to ship
2g	USD 250.00	Ready to ship
5g	USD 450.00	Ready to ship
10g	USD 750.00	Ready to ship
20g	USD 1,150.00	Ready to ship
50g	USD 1,750.00	Ready to ship
100g	USD 2,650.00	Ready to ship

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Related CAS #

No Data

Synonym

Accutane; Isotretinoin; Myorisan; Zenatane

IUPAC/Chemical Name

(2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid

InChi Key

SHGAZHPCJJPHSC-XFYACQKRSA-N

InChi Code

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-

SMILES Code

CC(/C=C/C=C(/C=C/C1=C(CCCC(C)1C)C)C)=C/C(O)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#A20T09K26

QC Data

View QC data: current batch, Lot#A20T09K26

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Isotretinoin(13-cis-Retinoic acid, 13-cis RA) targets RAR/RXR and is a medication used for the treatment of severe acne.

In vitro activity:

To assess whether 13-cis RA alters gene expression in human meibomian gland cells, cells were treated with vehicle or 2 μM 13-cis RA for 4 days (n = 3/group) and then processed the RNA for evaluation. The analysis demonstrated that 13-cis RA significantly (P < 0.05) altered the expression of thousands of genes (3520 ↑; 3206 ↓) in human meibomian gland epithelial cells. As shown in Table 1, these included an upregulation of genes for various inflammatory mediators (e.g., IL-36γ, IL-15, IL-8, and IL-1β) and proteases (e.g., matrix metallopeptidase 9 [MMP-9]), and a downregulation of genes for tyrosine kinase signaling (e.g., nerve growth factor b) and cell division (e.g., cell division cycle 25 homolog C). Exposure to 13-cis RA had a marked effect on many Kyoto Encyclopedia of Genes and Genomes (KEGG) pathways, biological processes, molecular functions, and cellular components in human meibomian gland epithelial cells. As demonstrated in Table 2, 13-cis RA enhanced the expression of genes related to lysosomes, mitogenactivated protein kinase signaling, apoptosis, cell death, and lytic vacuoles. 13-cis RA also upregulated the activity of six genes associated with keratinization (e.g., small proline-rich proteins SPRRs 2F, 2D, and 1B). Conversely, 13-cis RA suppressed genes in processes linked to DNA replication, cell cycle, RNA transport and binding, and mitochondria. Reference: Invest Ophthalmol Vis Sci. 2013 Jun; 54(6): 4341–4350. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3694789/

In vivo activity:

Reduced formation of N-ret-PE in treated retinas suggests that isotretinoin may inhibit accumulation of A2E. To test this possibility, isotretinoin was administered at 40 mg/kg per day via osmotic pump to 3-month-old abcr−/− mice. After 1 month, the mice were killed and the levels of A2PE-H2 and A2E in RPE were determined by HPLC. In untreated abcr−/− mice or mice treated with DMSO vehicle alone, A2PE-H2 increased ≈2.7-fold in the period between 3 and 4 months (Fig.4A). A2E increased 2.3-fold in DMSOtreated controls during the same period (Fig.4B). However, the levels of both A2PE-H2 and A2E virtually were unchanged from the levels at 3 months in mice that received isotretinoin (Fig.4). These data suggest that treatment with isotretinoin suppresses A2PE-H2 and A2E accumulation. Reference: Proc Natl Acad Sci U S A. 2003 Apr 15; 100(8): 4742–4747. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC153626/

	Solvent	mg/mL	mM
Solubility
	DMSO	54.0	179.74

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 300.44 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Nelson AM, Gilliland KL, Cong Z, Thiboutot DM. 13-cis Retinoic acid induces apoptosis and cell cycle arrest in human SEB-1 sebocytes. J Invest Dermatol. 2006 Oct;126(10):2178-89. doi: 10.1038/sj.jid.5700289. Epub 2006 Mar 30. PMID: 16575387. 2. Ding J, Kam WR, Dieckow J, Sullivan DA. The influence of 13-cis retinoic acid on human meibomian gland epithelial cells. Invest Ophthalmol Vis Sci. 2013 Jun 26;54(6):4341-50. doi: 10.1167/iovs.13-11863. PMID: 23722388; PMCID: PMC3694789. 3. Crandall J, Sakai Y, Zhang J, Koul O, Mineur Y, Crusio WE, McCaffery P. 13-cis-retinoic acid suppresses hippocampal cell division and hippocampal-dependent learning in mice. Proc Natl Acad Sci U S A. 2004 Apr 6;101(14):5111-6. doi: 10.1073/pnas.0306336101. Epub 2004 Mar 29. PMID: 15051884; PMCID: PMC387382 4. Radu RA, Mata NL, Nusinowitz S, Liu X, Sieving PA, Travis GH. Treatment with isotretinoin inhibits lipofuscin accumulation in a mouse model of recessive Stargardt's macular degeneration. Proc Natl Acad Sci U S A. 2003 Apr 15;100(8):4742-7. doi: 10.1073/pnas.0737855100. Epub 2003 Apr 1. PMID: 12671074; PMCID: PMC153626.

In vitro protocol:

In vivo protocol:

1. Crandall J, Sakai Y, Zhang J, Koul O, Mineur Y, Crusio WE, McCaffery P. 13-cis-retinoic acid suppresses hippocampal cell division and hippocampal-dependent learning in mice. Proc Natl Acad Sci U S A. 2004 Apr 6;101(14):5111-6. doi: 10.1073/pnas.0306336101. Epub 2004 Mar 29. PMID: 15051884; PMCID: PMC387382 2. Radu RA, Mata NL, Nusinowitz S, Liu X, Sieving PA, Travis GH. Treatment with isotretinoin inhibits lipofuscin accumulation in a mouse model of recessive Stargardt's macular degeneration. Proc Natl Acad Sci U S A. 2003 Apr 15;100(8):4742-7. doi: 10.1073/pnas.0737855100. Epub 2003 Apr 1. PMID: 12671074; PMCID: PMC153626.

1: Dalal A, Ben-Barak S, Zlotogorski A, Constantini N. [Isotretinoin and exercise: can the two walk together?]. Harefuah. 2014 Feb;153(2):104-8, 125. Review. Hebrew. PubMed PMID: 24716429. 2: Kızılyel O, Metin MS, Elmas ÖF, Çayır Y, Aktaş A. Effects of oral isotretinoin on lipids and liver enzymes in acne patients. Cutis. 2014 Nov;94(5):234-8. PubMed PMID: 25474452. 3: Webster GF, Leyden JJ, Gross JA. Results of a Phase III, double-blind, randomized, parallel-group, non-inferiority study evaluating the safety and efficacy of isotretinoin-Lidose in patients with severe recalcitrant nodular acne. J Drugs Dermatol. 2014 Jun;13(6):665-70. PubMed PMID: 24918555. 4: Rademaker M. Isotretinoin: dose, duration and relapse. What does 30 years of usage tell us? Australas J Dermatol. 2013 Aug;54(3):157-62. doi: 10.1111/j.1440-0960.2012.00947.x. Epub 2012 Sep 26. Review. PubMed PMID: 23013115. 5: Prevost N, English JC. Isotretinoin: update on controversial issues. J Pediatr Adolesc Gynecol. 2013 Oct;26(5):290-3. Review. PubMed PMID: 24147278. 6: Yilmaz Tasdelen O, Yurdakul FG, Duran S, Bodur H. Isotretinoin-induced arthritis mimicking both rheumatoid arthritis and axial spondyloarthritis. Int J Rheum Dis. 2015 May;18(4):466-9. doi: 10.1111/1756-185X.12464. Epub 2014 Oct 8. PubMed PMID: 25294249. 7: Lee HE, Chang IK, Lee Y, Kim CD, Seo YJ, Lee JH, Im M. Effect of antihistamine as an adjuvant treatment of isotretinoin in acne: a randomized, controlled comparative study. J Eur Acad Dermatol Venereol. 2014 Dec;28(12):1654-60. doi: 10.1111/jdv.12403. Epub 2014 Feb 21. PubMed PMID: 25081735. 8: Wolverton SE, Harper JC. Important controversies associated with isotretinoin therapy for acne. Am J Clin Dermatol. 2013 Apr;14(2):71-6. doi: 10.1007/s40257-013-0014-z. Review. PubMed PMID: 23559397. 9: Nagler AR, Orlow SJ. Dermatologists' attitudes, prescription, and counseling patterns for isotretinoin: a questionnaire-based study. J Drugs Dermatol. 2015 Feb;14(2):184-9. PubMed PMID: 25689814. 10: Gürbüz A, Özhan G, Güngör S, Erdal MS. Colloidal carriers of isotretinoin for topical acne treatment: skin uptake, ATR-FTIR and in vitro cytotoxicity studies. Arch Dermatol Res. 2015 Sep;307(7):607-15. doi: 10.1007/s00403-015-1566-y. Epub 2015 Apr 23. PubMed PMID: 25903443. 11: Lee YH, Scharnitz TP, Muscat J, Chen A, Gupta-Elera G, Kirby JS. Laboratory Monitoring During Isotretinoin Therapy for Acne: A Systematic Review and Meta-analysis. JAMA Dermatol. 2016 Jan;152(1):35-44. doi: 10.1001/jamadermatol.2015.3091. Review. Erratum in: JAMA Dermatol. 2016 Jan;152(1):114. PubMed PMID: 26630323. 12: Hoover KB, Miller CG, Galante NC, Langman CB. A double-blind, randomized, Phase III, multicenter study in 358 pediatric subjects receiving isotretinoin therapy demonstrates no effect on pediatric bone mineral density. Osteoporos Int. 2015 Oct;26(10):2441-7. doi: 10.1007/s00198-015-3158-2. Epub 2015 May 9. PubMed PMID: 25956286. 13: Rubio-García L, Pulido-Díaz N, Jímenez-López JL. [Isotretinoin and depressive symptoms in patiens with severe and recurrent acne]. Rev Med Inst Mex Seguro Soc. 2015;53 Suppl 1:S54-9. Spanish. PubMed PMID: 26020665. 14: Yıldızgören MT, Rifaioğlu EN, Demirkapı M, Ekiz T, Micooğulları A, Şen T, Turhanoğlu AD. Isotretinoin treatment in patients with acne vulgaris: does it impact muscle strength, fatigue, and endurance? Cutis. 2015 Jul;96(1):33-6. PubMed PMID: 26244352. 15: Yuksel N, Ozer MD, Akcay E, Ozen U, Uzun S. Reduced central corneal thickness in patients with isotretinoin treatment. Cutan Ocul Toxicol. 2015;34(4):318-21. doi: 10.3109/15569527.2014.990155. Epub 2015 Jan 19. PubMed PMID: 25597375. 16: Blasiak RC, Stamey CR, Burkhart CN, Lugo-Somolinos A, Morrell DS. High-dose isotretinoin treatment and the rate of retrial, relapse, and adverse effects in patients with acne vulgaris. JAMA Dermatol. 2013 Dec;149(12):1392-8. doi: 10.1001/jamadermatol.2013.6746. PubMed PMID: 24173086. 17: Pinheiro SP, Kang EM, Kim CY, Governale LA, Zhou EH, Hammad TA. Concomitant use of isotretinoin and contraceptives before and after iPledge in the United States. Pharmacoepidemiol Drug Saf. 2013 Dec;22(12):1251-7. doi: 10.1002/pds.3481. Epub 2013 Aug 3. PubMed PMID: 23913625. 18: Bilgiç Ö, Altınyazar HC, Sivrikaya A, Ünlü A. The relationship between erythrocyte zinc levels and isotretinoin use in acne vulgaris patients. Cutan Ocul Toxicol. 2015;34(4):303-6. doi: 10.3109/15569527.2014.979426. Epub 2014 Nov 6. PubMed PMID: 25373485. 19: Rouzès A, Jonville-Béra AP. [Exposure to isotretinoin during pregnancy in France: 25 years of follow-up]. Therapie. 2014 Jan-Feb;69(1):53-63. doi: 10.2515/therapie/2014008. Epub 2014 Apr 4. French. PubMed PMID: 24698189. 20: Eichenfield LF, Krakowski AC. A novel patient support program to address isotretinoin adherence: proof-of-concept analysis. J Drugs Dermatol. 2015 Apr;14(4):375-9. PubMed PMID: 25844611.