METHOCARBAMOL

First approved in 1957

Details

Stereochemistry	RACEMIC
Molecular Formula	C11H15NO5
Molecular Weight	241.2405
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C(OCC(O)COC(N)=O)C=CC=C1

InChI

InChIKey=GNXFOGHNGIVQEH-UHFFFAOYSA-N

InChI=1S/C11H15NO5/c1-15-9-4-2-3-5-10(9)16-6-8(13)7-17-11(12)14/h2-5,8,13H,6-7H2,1H3,(H2,12,14)

HIDE SMILES / InChI

Description
Sources: http://www.drugbank.ca/drugs/DB00423
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/methocarbamol.html

Methocarbamol is a central muscle relaxant for skeletal muscles, used to treat spasms. It is structurally related to guaifenesin. Methocarbamol's exact mechanism of causing skeletal muscle relaxation is unknown. It is thought to work centrally, perhaps by general depressant effects. It has no direct relaxant effects on striated muscle, nerve fibers, or the motor endplate. It will not directly relax contracted skeletal muscles. The drug has a secondary sedative effect. Methocarbamol is used for use as an adjunct to rest, physical therapy, and other measures for the relief of discomforts associated with acute, painful musculoskeletal conditions. Under the trade name Robaxin, Methocarbamol is marketed by Actient Pharmaceuticals in the United States and Pfizer in Canada.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Carbonic anhydrase I 62 Target ID: CHEMBL261 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1460006	Inhibitor 8297		70.0 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Muscle spasm 40 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2003/011011s070s071lbl.pdf	Palliative		Approved 8429	Robaxin Approved Use Robaxin® and robaxin®-750 are indicated as an adjunct to rest, physical therapy, and other measures for the relief of discomfort associated with acute, painful musculoskeletal conditions. Launch Date 1957

C_max

Value	Dose	Co-administered	Analyte	Population
21.3 mg/L EXPERIMENT https://link.springer.com/article/10.1007%2FBF00280060	1.5 g single, oral dose: 1.5 g route of administration: Oral experiment type: SINGLE co-administered:		METHOCARBAMOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
28.7 mg/L EXPERIMENT https://link.springer.com/article/10.1007%2FBF00280060	1.5 g single, oral dose: 1.5 g route of administration: Oral experiment type: SINGLE co-administered:		METHOCARBAMOL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
52.5 mg × h/L EXPERIMENT https://link.springer.com/article/10.1007%2FBF00280060	1.5 g single, oral dose: 1.5 g route of administration: Oral experiment type: SINGLE co-administered:		METHOCARBAMOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
87.1 mg × h/L EXPERIMENT https://link.springer.com/article/10.1007%2FBF00280060	1.5 g single, oral dose: 1.5 g route of administration: Oral experiment type: SINGLE co-administered:		METHOCARBAMOL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.14 h EXPERIMENT https://link.springer.com/article/10.1007%2FBF00280060	1.5 g single, oral dose: 1.5 g route of administration: Oral experiment type: SINGLE co-administered:		METHOCARBAMOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1.24 h EXPERIMENT https://link.springer.com/article/10.1007%2FBF00280060	1.5 g single, oral dose: 1.5 g route of administration: Oral experiment type: SINGLE co-administered:		METHOCARBAMOL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
52% EXPERIMENT https://link.springer.com/article/10.1007%2FBF00280060	1.5 g single, oral dose: 1.5 g route of administration: Oral experiment type: SINGLE co-administered:		METHOCARBAMOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
51.9% EXPERIMENT https://link.springer.com/article/10.1007%2FBF00280060	1.5 g single, oral dose: 1.5 g route of administration: Oral experiment type: SINGLE co-administered:		METHOCARBAMOL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
Nav1.7 36

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
Nav1.7 36	inhibitor 3277 Sources: https://onlinelibrary.wiley.com/doi/pdfdirect/10.1002/mus.27087	no

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY558816	https://www.001chemical.com/chem/532-03-6
3B Scientific (Wuhan) Corp	3B1-00244	http://www.3bsc.com/index/pro_info.php?id=20456
AA Blocks	AA00I9F1	https://www.aablocks.com/goods/Goods/detail?id=AA00I9F1
AK Scientific, Inc. (AKSCI)	67601	http://www.aksci.com/item_detail.php?cat=67601
Aaron Chemicals	AR00IA6T	http://www.aaronchem.com/532-03-6
AbMole Bioscience	M3349	http://www.abmole.com/products/methocarbamol.html
Alfa Chemistry	AP532036-A	https://reagents.alfa-chemistry.com/product/methocarbamol-cas-532-03-6-12650.html
Alfa Chemistry	AP532036-B	https://reagents.alfa-chemistry.com/product/methocarbamol-cas-532-03-6-12651.html
Alsachim	3969	http://www.alsachim.com/product-C5274-glo.bal-view.html
Anward	ANW-42701	http://www.anward.com/pro_result/25138
Ark Pharm	AK546751	http://www.arkpharminc.com/products/532-03-6.html
Aurora Fine Chemicals LLC	A00.761.137	http://online.aurorafinechemicals.com/info?ID=A00.761.137
Aurum Pharmatech LLC	NE28012	http://www.Aurumpharmatech.com/Product/ProductDetails/NE28012
BLD Pharm	BD137709	http://www.bldpharm.com/products/532-03-6.html
BioChemPartner	BCP13801	http://www.biochempartner.com/532-03-6-BCP13801
BioCrick	BCC3813	http://www.biocrick.com/Methyocarbamol-BCC3813.html
Boerchem	BC203907	http://www.boerchem.com/?product_34258.html
CSNpharm	CSN11395	https://www.csnpharm.com/products/methocarbamol.html
Capot Chemical	20751	http://www.capotchem.com/en/20751.htm
Capot Chemical	PubChem20751	http://www.capotchem.com/en/20751.htm
Chem Scene	CS-2248	http://www.chemscene.com/532-03-6.html
ChemMol	30101849	http://www.chemmol.com/chemmol/30101849.html
ChemMol	44001633	http://www.chemmol.com/chemmol/44001633.html
ChemMol	49416354	http://www.chemmol.com/chemmol/49416354.html
Chemenu	CM110530	http://www.chemenu.com/products/CM110530
Chemspace	CSSB00000693947	https://chem-space.com/CSSB00000693947
Clearsynth	CS-O-30645	https://www.clearsynth.com/en/CSO30645.html
Clearsynth	CS-T-57526	https://www.clearsynth.com/en/CST57526.html
Clearsynth	CS-T-57528	https://www.clearsynth.com/en/CST57528.html
Combi-Blocks	QH-6982	http://www.combi-blocks.com/cgi-bin/find.cgi?QH-6982
Finetech	FT-0671053	http://www.finetechnology-ind.com/prod/detail/pub/1189699-70-4.html
Finetech	FT-0628302	http://www.finetechnology-ind.com/prod/detail/pub/532-03-6.html
Glentham Life Sciences	GP1945	http://www.glentham.com/products/product/GP1945/
LGC Standards	DRE-C15028000	https://www.lgcstandards.com/US/en/p/DRE-C15028000
LGC Standards	LGCFOR1061.00	https://www.lgcstandards.com/US/en/p/LGCFOR1061.00
LGC Standards	MM1061.00	https://www.lgcstandards.com/US/en/p/MM1061.00
Lab Network	LN01306146	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01306146
MedChem Express	HY-B0262	https://www.medchemexpress.com/Methocarbamol.html
Molcore	MC558816	https://www.molcore.com/product/532-03-6
Parchem	18454	http://www.parchem.com/chemical-supplier-distributor/Methacarbamol-008454.aspx
Parchem	11000	http://www.parchem.com/chemical-supplier-distributor/Methocarbamol-001000.aspx
Renno Tech	RL03963	http://www.rennotech.com/product_show.asp?id=4283
Sigma-Aldrich	G7012_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/g7012?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	PHR1395_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/phr1395?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1412008_USP	https://www.sigmaaldrich.com/catalog/product/usp/1412008?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S535126	http://www.smolecule.com/products/s535126
Smolecule	S772582	https://www.smolecule.com/products/s772582
TCI (Tokyo Chemical Industry)	M2254	http://www.tcichemicals.com/eshop/en/us/commodity/M2254/index.html
THE BioTek	bt-275398	https://www.thebiotek.com/product/inhibitors/bt-275398
VladaChem	VL264583-25G	https://www.vladachem.com/product.php?products=532-03-6
Yuhao Chemical	LL0932	http://www.chemyuhao.com/532-03-6.html
abcr GmbH	AB505692	http://www.abcr.com/shop/en/AB505692
eNovation Chemicals	D674542	https://www.enovationchem.com/ProductDetails.asp?ProductID=D674542
eNovation Chemicals	D962388	https://www.enovationchem.com/ProductDetails.asp?ProductID=D962388
iChemical	EBD54978	http://www.ichemical.com/chemicals/cas-532-03-6
mcule	MCULE-7298838587	https://mcule.com/MCULE-7298838587/

PubMed

Title	Date	PubMed
Pharmacokinetics and protein binding of methocarbamol in renal insufficiency and normals.	1990	2253675
Focal seizure following enflurane.	1992 Jan	1536426
Carbonic anhydrase inhibitors: clash with Ala65 as a means for designing inhibitors with low affinity for the ubiquitous isozyme II, exemplified by the crystal structure of the topiramate sulfamide analogue.	2006 Nov 30	17125255

Patents

Sample Use Guides

In Vivo Use Guide

Usual Adult Dose for Muscle Spasm Oral: Initial dose: 1500 mg four times a day for the first 48 to 72 hours, up to a maximum dosage of 8 g/day for severe symptoms. Maintenance dose: 4000 to 4500 mg/day in divided doses. IV or IM: 1000 mg up to every 8 hours if necessary, not to exceed 3 g/day for more than 3 consecutive days except in the treatment of tetanus. A like course may be repeated after a lapse of 48 hours if the condition persists. Oral therapy should be instituted as soon as possible.

Route of Administration: Other

In Vitro Use Guide

Unknown

Name

Type

Language

METHOCARBAMOL

Official Name

English

ROBAXISAL COMPONENT METHOCARBAMOL

Common Name

English

1,2-PROPANEDIOL, 3-(2-METHOXYPHENOXY)-, 1-CARBAMATE, (±)-

Common Name

English

NSC-170960

Code

English

(±)-3-(O-METHOXYPHENOXY)-1,2-PROPANEDIOL 1-CARBAMATE

Common Name

English

DELAXIN

Brand Name

English

METHOCARBAMOL [MART.]

Common Name

English

ROBAXIN

Brand Name

English

FORBAXIN

Brand Name

English

METHOCARBAMOL [MI]

Common Name

English

methocarbamol [INN]

Common Name

English

METHOCARBAMOL [VANDF]

Common Name

English

METHOCARBAMOL [ORANGE BOOK]

Common Name

English

METHOCARBAMOL [JAN]

Common Name

English

METHOCARBAMOL [USP MONOGRAPH]

Common Name

English

METHOCARBAMOL COMPONENT OF ROBAXISAL

Common Name

English

Methocarbamol [WHO-DD]

Common Name

English

METHOCARBAMOL [GREEN BOOK]

Common Name

English

METHOCARBAMOL [USP-RS]

Common Name

English

METHOCARBAMOL [HSDB]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29696