Drug Information

General Information
Drug ID
DR00036
Drug Name
Cholesterol
Synonyms
(-)-Cholesterol; (3beta)-cholest-5-en-3-ol; 3-beta-Hydroxycholest-5-ene; 3beta-Hydroxycholest-5-ene; 5-Cholesten-3beta-ol; 5:6-Cholesten-3beta-ol; CCRIS 2834; Cholest-5-en-3-beta-ol; Cholest-5-en-3-ol (3beta)-; Cholest-5-en-3beta-ol; Cholesterin; Cholesterine; Cholesterol base H; Cholesteryl alcohol; Cholestrin; Cholestrol; Cordulan; Dastar; Dusoline; Dusoran; Dythol; HSDB 7; Hydrocerin; Kathro; Lanol; Lidinit; Lidinite; Nimco cholesterol base H; Provitamin D; Super hartolan; Tegolan; Tegolan (VAN); Wool alcohols B. P.
Drug Type
Small molecular drug
Indication Cone-Rod dystrophy [ICD11:9B70] Phase 2 [1]
Structure
3D MOL 2D MOL
Formula
C27H46O
Canonical SMILES
CC(C)CCCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C
InChI
InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1
InChIKey
HVYWMOMLDIMFJA-DPAQBDIFSA-N
CAS Number
CAS 17528-72-2
Pharmaceutical Properties Molecular Weight 386.7 Topological Polar Surface Area 20.2
Heavy Atom Count 28 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 1
XLogP
8.7
PubChem CID
5997
PubChem SID
10318723 ,10586602 ,12159193 ,14927473 ,15054036 ,2231 ,24848759 ,24852491 ,24856217 ,24856220 ,24870712 ,24892329 ,24892335 ,24892388 ,24893064 ,24893094 ,24899653 ,25621399 ,26750557 ,26754461 ,29203946 ,29215267 ,29225011 ,3132495 ,3487 ,4266362 ,46393729 ,47211564 ,47722068 ,48421907 ,49684278 ,49688267 ,49786946 ,49833611 ,49854209 ,49903086 ,53787861 ,56311936 ,57323103 ,57647874 ,629186 ,74414 ,7847108 ,7886645 ,8025561 ,8145005 ,8153730 ,825929 ,827331 ,841782
ChEBI ID
ChEBI:15372
TTD Drug ID
D02DLW
DT(s) Transporting This Drug ABCA1 Transporter Info ATP-binding cassette sub-family A member 1 Substrate [2]
ABCA12 Transporter Info ATP-binding cassette sub-family A member 12 Substrate [3]
ABCA2 Transporter Info ATP-binding cassette sub-family A member 2 Substrate [4]
ABCA5 Transporter Info ATP-binding cassette sub-family A member 5 Substrate [5]
ABCG1 Transporter Info ATP-binding cassette sub-family G member 1 Substrate [6]
BCRP Transporter Info Breast cancer resistance protein Substrate [7]
NPC1L1 Transporter Info Niemann-Pick C1-like protein 1 Substrate [8]
P-GP Transporter Info P-glycoprotein 1 Substrate [9]
References
1 ClinicalTrials.gov (NCT01773278) Cholesterol and Antioxidant Treatment in Patients With Smith-Lemli-Opitz Syndrome (SLOS)
2 ABCA1 redistributes membrane cholesterol independent of apolipoprotein interactions. J Lipid Res. 2003 Jul;44(7):1373-80.
3 ABCA12 regulates ABCA1-dependent cholesterol efflux from macrophages and the development of atherosclerosis. Cell Metab. 2013 Aug 6;18(2):225-38.
4 The ATP-binding cassette transporter-2 (ABCA2) regulates cholesterol homeostasis and low-density lipoprotein receptor metabolism in N2a neuroblastoma cells. Biochim Biophys Acta. 2011 Dec;1811(12):1152-64.
5 Mutations in the cholesterol transporter gene ABCA5 are associated with excessive hair overgrowth. PLoS Genet. 2014 May 15;10(5):e1004333.
6 Role of HDL, ABCA1, and ABCG1 transporters in cholesterol efflux and immune responses. Arterioscler Thromb Vasc Biol. 2010 Feb;30(2):139-43.
7 Sterol transport by the human breast cancer resistance protein (ABCG2) expressed in Lactococcus lactis. J Biol Chem. 2003 Jun 6;278(23):20645-51.
8 Niemann-Pick C1 Like 1 protein is critical for intestinal cholesterol absorption. Science. 2004 Feb 20;303(5661):1201-4.
9 Cholesterol interaction with the daunorubicin binding site of P-glycoprotein. Biochem Biophys Res Commun. 2000 Oct 5;276(3):909-16.

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