4-Hydroxybutanoic acid
- 4-Hydroxybutanoic acid
- 4-Hydroxybutyric acid
- gamma-Hydroxybutyric acid
- 591-81-1
- gamma-Hydroxybutyrate
- Create:2004-09-16
- Modify:2025-01-18
- 4-hydroxybutyric acid
- gamma-hydroxybutyric acid
- 4-Hydroxybutanoic acid
- 4-Hydroxybutyric acid
- gamma-Hydroxybutyric acid
- 591-81-1
- gamma-Hydroxybutyrate
- Xyrem
- 4-hydroxy-butyric acid
- Oxybate
- Butanoic acid, 4-hydroxy-
- Gamma Hydroxybutyric Acid
- 4-hydroxy-butanoic acid
- GHB
- oxy-n-butyric acid
- Butyric acid, 4-hydroxy-
- Oxybate sodium
- 3-carboxypropoxy acid
- 4-Hydroxyalkanoic acid
- 4-Hydroxycarboxylic acid
- Somsanit
- gamma Hydroxybutyrate
- 4-Hydroxybutyrate sodium
- .gamma.-hydroxybutyrate
- Gamma OH
- Gam-OH
- CHEMBL1342
- CHEBI:30830
- 4-Hydroxybutyric acid monosodium salt
- Sodium .gamma.-oxybutyrate
- 30IW36W5B2
- 4-OHB
- Sodium .gamma.-hydroxybutyrate
- 4 HB
- 4-Hydroxybuttersaeure
- EB 27
- .gamma.-OH
- WY 3478
- WY-3478
- gamma-Hydroxybutanoic acid
- 4-Hydroxyacid
- .gamma.-Hydroxybutyrate sodium
- .gamma.-Hydroxy sodium butyrate
- Hydroxybutyric acid monosodium salt
- NSC84223
- gamma-hydroxy butyrate
- .gamma.-Hydroxybutyric acid, sodium salt
- NCGC00247714-01
- SHB
- .gamma.-Hydroxybutyric acid monosodium salt
- BRN 1720582
- Alcover
- UNII-30IW36W5B2
- 52352-27-9
- HSDB 6927
- Hydroxybutyric acid-
- Sodium gamma-oxybutyrate
- .Gamma.-Hydroxy butyrate
- 4-Hydroxybutanoic acid #
- SCHEMBL10786
- 4-03-00-00774 (Beilstein Handbook Reference)
- GTPL4711
- DEA No. 2010
- AA3E2AF0-AB7A-4A1E-A391-199C049D7162
- DTXSID2074740
- .GAMMA.-HYDROXYBUTYRIC ACID
- BDBM50023575
- LMFA01050006
- PDSP1_000342
- PDSP2_000340
- .GAMMA.-HYDROXYBUTYRATE [MI]
- GAMMA-HYDROXYBUTYRATE [WHO-DD]
- DB01440
- GAMMA-HYDROXYBUTYRIC ACID [HSDB]
- SBI-0206686.P002
- NS00002886
- C00989
- C01991
- 4-Hydroxybutanoic acid (sold as SODIUM OXYBATE)
- Q207920
- BRD-K82166906-236-02-8
116.04 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
124.34 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
117.0 1
233.0 0.47
143.0 0.21
103.0 0.19
133.0 0.18
147.0 100
117.0 31.43
233.0 17.82
148.0 16.72
149.0 8.61
57.0 100
103.0 100
85.0 100
103.0399 92.82
85.0294 5.20
101.0244 1.98
57 100
85 100
103 100
(Street Names:GHB, G, Liquid Ecstasy, Liquid X, Liquid G, Goop, Georgia Home Boy, Grievous Bodily Harm, Easy Lay)
apparent oral cl=9.1 mL/min/kg [healthy adults receiving a single oral dose of 25 mg/kg]
4.5 mL/min/kg [cirrhotic patients without ascites receiving a single oral dose of 25 mg/kg]
4.1 mL/min/kg [cirrhotic patients with ascites receiving a single oral dose of 25 mg/kg]
Use (kg; approx.) in Germany (2009): >750
Consumption (g per capita; approx.) in Germany (2009): 0.00916
Excretion rate: 0.01
Calculated removal (%): 92.1
Not Classified
Reported as not meeting GHS hazard criteria by 2 of 2 companies. For more detailed information, please visit ECHA C&L website.
Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.
Reported as not meeting GHS hazard criteria per 2 of 2 reports by companies. For more detailed information, please visit ECHA C&L website.
There are 0 notifications provided by 0 of 2 reports by companies with hazard statement code(s).
Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.
In preregistration clinical trials, serum enzyme elevations were reported in small numbers of treated patients, but no instance of clinically apparent liver injury was reported. Since the approval and more widespread use of oxybate, there have been no published cases of liver injury due to oxybate, and in postmarketing overviews of adverse events hepatotoxicity was not listed. Thus, despite use in high doses (3 to 9 g daily), acute liver injury from oxybate must be very rare, if it occurs at all.
Likelihood score: E (unlikely cause of clinically apparent liver injury).
M Chen, V Vijay, Q Shi, Z Liu, H Fang, W Tong. FDA-Approved Drug Labeling for the Study of Drug-Induced Liver Injury, Drug Discovery Today, 16(15-16):697-703, 2011. PMID:21624500 DOI:10.1016/j.drudis.2011.05.007
M Chen, A Suzuki, S Thakkar, K Yu, C Hu, W Tong. DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans. Drug Discov Today 2016, 21(4): 648-653. PMID:26948801 DOI:10.1016/j.drudis.2016.02.015
◉ Summary of Use during Lactation
Sodium, calcium, magnesium and potassium oxybate are salts of gamma-hydroxybutyric acid (GHB). GHB is an endogenous substance and low amounts are normally found in breastmilk. Large doses of GHB have been used as a substance of abuse. Infants have been successfully breastfed by mothers taking sodium oxybate therapeutically for narcolepsy. With the typical 2 doses per night treatment regimen, nursing should usually be withheld from the time of the first dose to 4 to 6 hours after the second dose and breastfeeding can be continued during the day. No information is available on the use or safety of GHB as a drug of abuse during breastfeeding. Monitor the infant for sedation, poor feeding and poor weight gain.
◉ Effects in Breastfed Infants
A woman was taking 4.5 grams of sodium oxybate twice daily (exact times not reported) for narcolepsy and cataplexy throughout pregnancy and lactation. She breastfed her infant (extent and times not stated). No adverse infant effects were reported.
A woman with narcolepsy took sodium oxybate 4 grams each night at 10 pm and 2 am as well as fluoxetine 20 mg and cetirizine 5 mg daily throughout pregnancy and postpartum. She breastfed her infant except for 4 hours after the 10 pm oxybate dose and 4 hours after the 2 am dose. She either pumped breastmilk or breastfed her infant just before each dose of oxybate. The infant was exclusively breastfed or breastmilk fed for 6 months when solids were introduced. The infant was evaluated at 2, 4 and 6 months with the Ages and Stages Questionnaires, which were withing the normal range as were the infant's growth and pediatrician's clinical impressions regarding the infant's growth and development.
◉ Effects on Lactation and Breastmilk
Relevant published information was not found as of the revision date.
PubMed: 12127325, 14595661, 11978597
MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Silke Matysik, Caroline Ivanne Le Roy, Gerhard Liebisch, Sandrine Paule Claus. Metabolomics of fecal samples: A practical consideration. Trends in Food Science & Technology. Vol. 57, Part B, Nov. 2016, p.244-255: http://www.sciencedirect.com/science/article/pii/S0924224416301984
PubMed: 6158623, 24453145, 16388731
MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=SJZRECIVHVDYJC-UHFFFAOYSA-N
- CAS Common ChemistryLICENSEThe data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.https://creativecommons.org/licenses/by-nc/4.0/4-Hydroxybutyric acidhttps://commonchemistry.cas.org/detail?cas_rn=591-81-1Poly(4-hydroxybutyrate)https://commonchemistry.cas.org/detail?cas_rn=114959-05-6Poly(hydroxybutyrate)https://commonchemistry.cas.org/detail?cas_rn=52352-27-9
- ChemIDplusgamma-Hydroxybutyric acidhttps://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000591811ChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- DrugBankLICENSECreative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)https://www.drugbank.ca/legal/terms_of_usegamma-Hydroxybutyric acidhttps://www.drugbank.ca/drugs/DB01440
- EPA DSSTox4-Hydroxybutyric acidhttps://comptox.epa.gov/dashboard/DTXSID2074740CompTox Chemicals Dashboard Chemical Listshttps://comptox.epa.gov/dashboard/chemical-lists/
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- Natural Product Activity and Species Source (NPASS)
- West Coast Metabolomics Center-UC Davis4-Hydroxybutyric acid
- EU Clinical Trials Register
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- SpectraBase4-Hydroxybutanoic acidhttps://spectrabase.com/spectrum/H19xGnk9Eg4gamma-Hydroxybutyric acidhttps://spectrabase.com/spectrum/DlgROGmoecyGHB;4-HYDROXY-BUTANOIC-ACID;GAMMA-HYDROXY-BUTYRIC-ACIDhttps://spectrabase.com/spectrum/DvDHPd9hBy8
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