Details of the Drug

General Information of Drug (ID: DMGBKVD)

Drug Name
Gamma hydroxybutyric acid
Synonyms
Anetamin; GHB; Hydroxyb; Oxybate; SHB; Somsanit; Xyrem; Gamma OH; Oxybate sodium; Utyric acid monosodium salt; EB 27; WY 3478; Gam-OH; Gamma-Hydroxy butyrate; Gamma-Hydroxy sodium butyrate; Gamma-Hydroxybutanoic acid; Gamma-Hydroxybutyrate sodium; Gamma-Hydroxybutyric acid; Gamma-Hydroxybutyric acid decomposition product; Gamma-Hydroxybutyric acid monosodium salt; Gamma-OH; Xyrem (TN); Gamma-Hydroxybutyric acid, sodium salt; Oxy-n-butyric acid; Sodium Oxybate (4-hydroxybutanoic acid); Sodium .gamma.-hydroxybutyrate; Sodium .gamma.-oxybutyrate; AA3E2AF0-AB7A-4A1E-A391-199C049D7162; Butanoic acid, 4-hydroxy-, monosodium salt; Butanoic acid, 4-hydroxy-, sodium salt; Butyric acid, 4-hydroxy-, monosodium salt; Butyric acid, 4-hydroxy-, sodium salt; 3-carboxypropoxy acid; 4 HB; 4-Hydroxy; 4-Hydroxyacid; 4-Hydroxyalkanoic acid; 4-Hydroxybutanoic acid; 4-Hydroxybuttersaeure; 4-Hydroxybutyrate sodium; 4-Hydroxybutyric acid; 4-Hydroxybutyric acid monosodium salt; 4-Hydroxycarboxylic acid; 4-OHB; 4-hydroxy-butyric acid
Indication
Disease Entry ICD 11 Status REF
Narcolepsy 7A20 Approved [1], [2]
Therapeutic Class
Anesthetics
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 104.1
Topological Polar Surface Area (xlogp) -0.6
Rotatable Bond Count (rotbonds) 3
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 3
ADMET Property
Clearance
The apparent oral clearance of drug is 9.1 mL/min/kg [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 30 - 60 minutes [4]
Vd
The volume of distribution (Vd) of drug is 0.19-0.384 L/kg [3]
Chemical Identifiers
Formula
C4H8O3
IUPAC Name
4-hydroxybutanoic acid
Canonical SMILES
C(CC(=O)O)CO
InChI
InChI=1S/C4H8O3/c5-3-1-2-4(6)7/h5H,1-3H2,(H,6,7)
InChIKey
SJZRECIVHVDYJC-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
10413
ChEBI ID
CHEBI:30830
CAS Number
591-81-1
TTD ID
D0EP8X
VARIDT ID
DR00987

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Gamma-aminobutyric acid B receptor (GABBR) TTDCVZW GABR1_HUMAN; GABR2_HUMAN Modulator [5]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Sodium-coupled monocarboxylate transporter 2 (SLC5A12) DTM301H SC5AC_HUMAN Substrate [6]
Monocarboxylate transporter 1 (SLC16A1) DT342ZG MOT1_HUMAN Substrate [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

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2 Sodium oxybate: a review of its use in the management of narcolepsy. CNS Drugs. 2007;21(4):337-54.
3 An FDA phase I clinical trial of quinacrine sterilization (QS). Int J Gynaecol Obstet. 2003 Oct;83 Suppl 2:S45-9.
4 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
6 Sodium-coupled monocarboxylate transporters in normal tissues and in cancer. AAPS J. 2008;10(1):193-9.
7 Flavonoids modulate monocarboxylate transporter-1-mediated transport of gamma-hydroxybutyrate in vitro and in vivo. Drug Metab Dispos. 2007 Feb;35(2):201-8.
8 Circadian rhythms in gene expression: Relationship to physiology, disease, drug disposition and drug action. Adv Drug Deliv Rev. 2010 Jul 31;62(9-10):904-17.
9 H+-coupled nutrient, micronutrient and drug transporters in the mammalian small intestine. Exp Physiol. 2007 Jul;92(4):603-19.
10 AR-C155858 is a potent inhibitor of monocarboxylate transporters MCT1 and MCT2 that binds to an intracellular site involving transmembrane helices 7-10. Biochem J. 2010 Jan 15;425(3):523-30.
11 Overview of the proton-coupled MCT (SLC16A) family of transporters: characterization, function and role in the transport of the drug of abuse gamma-hydroxybutyric acid. AAPS J. 2008 Jun;10(2):311-21.
12 Interaction of atorvastatin with the human glial transporter SLC16A1. Eur J Pharmacol. 2016 Oct 5;788:248-254.
13 Cidofovir peptide conjugates as prodrugs. Journal of Organometallic Chemistry, 2005, 690(10):2673-2678.
14 Biotin. Biofactors. 2009 Jan-Feb;35(1):36-46.
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16 Gabapentin increases a tonic inhibitory conductance in hippocampal pyramidal neurons. Anesthesiology. 2006 Aug;105(2):325-33.
17 Synthesis and pharmacology of the baclofen homologues 5-amino-4-(4-chlorophenyl)pentanoic acid and the R- and S-enantiomers of 5-amino-3-(4-chlorop... J Med Chem. 1999 Jun 3;42(11):2053-9.
18 Interactions between dopamine and GABA in the control of ambulatory activity and neophobia in the mouse. Pharmacol Biochem Behav. 1998 Jan;59(1):239-47.
19 Arbaclofen placarbil, a novel R-baclofen prodrug: improved absorption, distribution, metabolism, and elimination properties compared with R-baclofen.J Pharmacol Exp Ther.2009 Sep;330(3):911-21.
20 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 242).
21 Impact of acamprosate on behavior and brain-derived neurotrophic factor: an open-label study in youth with fragile X syndrome. Psychopharmacology (Berl). 2013 Jul;228(1):75-84.
22 3-Thienyl- and 3-furylaminobutyric acids. Synthesis and binding GABAB receptor studies. J Med Chem. 1991 Aug;34(8):2557-60.
23 SGS742: the first GABA(B) receptor antagonist in clinical trials. Biochem Pharmacol. 2004 Oct 15;68(8):1479-87.
24 Reversal of disease-related pathologies in the fragile X mouse model by selective activation of GABAB receptors with arbaclofen. Sci Transl Med. 2012 Sep 19;4(152):152ra128.
25 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)