Isotretinoin

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Isotretinoin are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Isotretinoin?

The molecule Isotretinoin presents a molecular formula of C20H28O2 and its IUPAC name is (2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid.

Isotretinoin is a molecule used in the treatment of acne. It is a retinoid, meaning it comes from from vitamin A and works by decreasing the production of sebum, the oily substance that can block pores and lead to acne. Isotretinoin exists as a pill or a topical solution. It is typically taken once or twice a day for four to five months. Side effects can include dry skin, lips and eyes, and nosebleeds..

3D structure

Cartesian coordinates

Geometry of Isotretinoin in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Isotretinoin SHGAZHPCJJPHSC-XFYACQKRSA-N chemical compound 2D structure molecule svg
Isotretinoin

 

Molecule descriptors

 
IUPAC name(2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid
InChI codeInChI=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-
InChI KeySHGAZHPCJJPHSC-XFYACQKRSA-N
SMILESCC1=C(/C=C/C(C)=C/C=C/C(C)=C\C(=O)O)C(C)(C)CCC1

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (13-cis)-Retinoate
  • (13-cis)-Retinoic acid
  • (13cis)-retinoic acid
  • (2Z,4E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,4,6,8-nonatetraenoic acid
  • (2Z,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic Acid
  • (2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid
  • (2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
  • (2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoicacid
  • (2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid
  • (2Z,4E6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
  • (7E,9E,11E,13Z)-retinoic acid
  • 13 Cis-Retinoic Acid
  • 13-RA
  • 13-cis RA
  • 13-cis retinoic acid
  • 13-cis-Retinoic acid
  • 13-cis-Vitamin A acid
  • 13-cis-retinoic acid,Isotretinoin
  • 13cRA
  • 286464-92-4
  • 3,7-DIMETHYL-9-(2,6,6-TRIMETHYL-1-CYCLOHEXEN-1-YL)-2-CIS-4-TRANS-6-TRANS-8-TRANS-NONATETRAENOIC ACID
  • 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)2-cis-4-trans-6-trans-8-trans-nonatetraenoic acid
  • 4759-48-2
  • 59I482
  • A917531
  • ABSORICA LD
  • Absorica
  • Accutane
  • Amnesteem
  • BCP18950
  • BDBM50031459
  • BML2-E07
  • BPBio1_000080
  • BR164589
  • BRN 1885770
  • BSPBio_000072
  • BSPBio_001331
  • BSPBio_003345
  • C07058
  • CCG-205158
  • CCRIS 4286
  • CIP-Isotretinoin
  • CPD000471891
  • CS-1864
  • Claravis
  • D00348
  • DB00982
  • DS-3367
  • DSSTox_CID_3177
  • DSSTox_GSID_23177
  • DSSTox_RID_76906
  • EH28UP18IF
  • EU-0101081
  • GTPL7600
  • HMS1361C13
  • HMS1568D14
  • HMS1791C13
  • HMS1921D08
  • HMS1989C13
  • HMS2092N07
  • HMS2095D14
  • HMS2233A07
  • HMS3259J09
  • HMS3263I04
  • HMS3402C13
  • HMS3712D14
  • HMS3884A13
  • HSDB 3929
  • HY-15127
  • IDI1_033801
  • ISOTRETINON
  • Isosuprea Lidose
  • Isotane
  • Isotretinoin
  • Isotretinoine
  • Isotretinoinum
  • Isotrex
  • LMPR01090021
  • LP01081
  • Lopac0_001081
  • MFCD00079542
  • MLS001074662
  • Myorisan
  • NC00635
  • NCGC00094358-01
  • NCGC00094358-02
  • NCGC00094358-03
  • NCGC00094358-04
  • NCGC00094358-05
  • NCGC00094358-06
  • NCGC00094358-07
  • NCGC00094358-08
  • NCGC00094358-09
  • NCGC00094358-10
  • NCGC00094358-11
  • NCGC00094358-12
  • NCGC00094358-13
  • NCGC00094358-14
  • NCGC00094358-15
  • NCGC00094358-26
  • NCGC00257647-01
  • NCGC00261766-01
  • NSC 758156
  • NSC-758156
  • NSC758156
  • Neovitamin A acid
  • PAT-001
  • Pharmakon1600-01502013
  • Prestwick2_000256
  • Prestwick3_000256
  • Prestwick_642
  • Q287029
  • R 3255
  • R0088
  • RETINOIC ACID, 13-cis-
  • Retinoic acid 13-cis-form
  • Retinoic acid, (13cis)-
  • Retinoic acid, (9,13-cis)-
  • Ro 4-3780
  • Ro-4-3780
  • Ro-43780
  • Roaccutan
  • Roaccutane
  • Roacutan
  • SBI-0051051.P003
  • SDCCGSBI-0051051.P004
  • SMR000471891
  • SPECTRUM1502013
  • SR-01000076103
  • SR-01000076103-10
  • SR-01000076103-2
  • SR-01000076103-5
  • SR-01000076103-6
  • SR-01000076103-9
  • Sotret
  • Teriosal
  • Trans-Retinoicacid
  • Vitamin a acid, 13-cis
  • Zenatane
  • cis retinoic acid
  • cis-RA
  • cis-Retinoate
  • cis-Retinoic acid
  • isotretinoina
  • isotretinoino

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3792789
  • CAS-4759-48-2
  • UNII-EH28UP18IF
  • AKOS015841158
  • BRD-K76723084-001-05-9
  • DTXSID4023177
  • CHEMBL547
  • CHEBI:6067
  • Tox21_200093
  • Tox21_501081
  • EINECS 225-296-0
  • SCHEMBL38299
  • Spectrum5_001795
  • Spectrum5_001937

Physico-Chemical properties

IUPAC name(2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid
Molecular formulaC20H28O2
Molecular weight300.435
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity95.28
LogP5.6
Topological polar surface area37.3

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.