Tretinoin

Tretinoin
Clinical data
Pronunciation	See pronunciation note
Trade names	Retin-A, Avita, Renova, others
Other names	ATRA
AHFS/Drugs.com	Monograph; Topical Monograph
MedlinePlus	a608032
License data	US DailyMed: Tretinoin;
Pregnancy; category	AU: X (High risk)/ (Oral); D (Topical);
Routes of; administration	Topical, by mouth
ATC code	D10AD01 (WHO) L01XF01 (WHO), D10AD51 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C2 (Retinoids); UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Protein binding	> 95%
Elimination half-life	0.5–2 hours
Identifiers
	IUPAC name (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid;
CAS Number	302-79-4 ;
PubChem CID	444795;
IUPHAR/BPS	2644;
DrugBank	DB00755 ;
ChemSpider	392618 ;
UNII	5688UTC01R;
KEGG	D00094 ; C00777 ;
ChEBI	CHEBI:15367 ;
ChEMBL	ChEMBL38 ;
CompTox Dashboard (EPA)	DTXSID7021239 ;
ECHA InfoCard	100.005.573
Chemical and physical data
Formula	C20H28O2
Molar mass	300.442 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	180 °C (356 °F)
	SMILES CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC(=O)O)C)C;
	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+ ; Key:SHGAZHPCJJPHSC-YCNIQYBTSA-N dd><htt//60967409 Arsen Ramirez Cruzﺁ;
	(verify)

Tretinoin, also known as all-trans retinoic acid (ATRA), is a medication used for the treatment of acne and acute promyelocytic leukemia. For acne, it is applied to the skin as a cream, gel or ointment. For acute promyelocytic leukemia, it is effective only when the RARA-PML fusion mutation is present and is taken by mouth for up to three months. Topical tretinoin is also the most extensively investigated retinoid therapy for photoaging.

Common side effects when used as a cream are limited to the skin and include skin redness, peeling, and sun sensitivity. When taken by mouth, side effects include hypertriglyceridemia, hypercholesterolemia, shortness of breath, headache, numbness, depression, skin dryness, itchiness, hair loss, vomiting, muscle pains, and vision changes. Other severe side effects include high white blood cell counts and blood clots. Use during pregnancy is contraindicated due to the risk of birth defects. It is in the retinoid family of medications.

Tretinoin was patented in 1957 and approved for medical use in 1962. It is on the World Health Organization's List of Essential Medicines. Tretinoin is available as a generic medication. In 2022, it was the 238th most commonly prescribed medication in the United States, with more than 1 million prescriptions.