U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry EPIMERIC
Molecular Formula C16H21NO3.BrH
Molecular Weight 356.255
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HOMATROPINE HYDROBROMIDE

SMILES

Br.CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)C(O)C3=CC=CC=C3

InChI

InChIKey=DWSGTFTVBLXELC-RDYJJYPNSA-N
InChI=1S/C16H21NO3.BrH/c1-17-12-7-8-13(17)10-14(9-12)20-16(19)15(18)11-5-3-2-4-6-11;/h2-6,12-15,18H,7-10H2,1H3;1H/t12-,13+,14+,15?;

HIDE SMILES / InChI
Homatropine (used in a form of bromide or methylbromide salts) is an analogue of atropine, which acts as an antagonist of muscarinic receptors. Homatropine was approved for the treatment of cough in combination with hydrocodone bitartrate.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
HYDROCODONE BITARTRATE AND HOMATROPINE METHYLBROMIDE

Approved Use

Hydrocodone bitartrate and homatropine methylbromide syrup is indicated for the symptomatic relief of cough.

Launch Date

1983
PubMed

PubMed

TitleDatePubMed
Anticholinergic delirium caused by topical homatropine ophthalmologic solution: confirmation by anticholinergic radioreceptor assay in two cases.
1992 Spring
Buspirone, but not sumatriptan, induces miosis in humans: relevance for a serotoninergic pupil control.
1995 Mar
Herpes simplex virus type 1 associated acute retinal necrosis following encephalitis.
2001
Tris(2,2'-bipyridine)ruthenium(II) electrogenerated chemiluminescence of alkaloid type drugs with solid phase extraction sample preparation.
2001 Jan
Scavenging of photogenerated oxidative species by antimuscarinic drugs: atropine and derivatives.
2002
Human carboxylesterase 1: from drug metabolism to drug discovery.
2003 Jun
Structural basis of heroin and cocaine metabolism by a promiscuous human drug-processing enzyme.
2003 May
Corneal topographic changes following retinal surgery.
2004 Aug 3
Familial HLA-A2- and HLA-B7-associated anterior uveitis.
2004 Oct
Acute posterior multifocal placoid pigment epitheliopathy after meningococcal C conjugate vaccine.
2005 Apr
Frontotemporal dementia with co-occurrence of astrocytic plaques and tufted astrocytes, and severe degeneration of the cerebral white matter: a variant of corticobasal degeneration?
2005 Mar
Evaluation of amniotic membrane transplantation as an adjunct to medical therapy as compared with medical therapy alone in acute ocular burns.
2005 Nov
Homatropine and psychosis in Weill-Marchesani syndrome.
2006 Jul
Increasing the scale of true moving bed electrophoretic separations using filtration to reduce solvent volumetric flows between sections II and III.
2007 Jan 5
Capillary electrophoresis of tropane alkaloids and glycoalkaloids occurring in Solanaceae plants.
2008
Granuloma annulare anterior uveitis.
2008 Jan-Feb
Hypotony maculopathy in a patient with HLA-B27-associated uveitis.
2008 May-Jun
Voriconazole for the treatment of refractory Aspergillus fumigatus keratitis.
2008 May-Jun
Keratouveitis caused by Euphorbia plant sap.
2009 Jul-Aug
Adverse drug effects in hospitalized elderly: data from the healthcare cost and utilization project.
2010
Tubulointerstitial nephritis with uveitis syndrome: A case report and review of literature.
2010 Apr
Is homatropine 5% effective in reducing pain associated with corneal abrasion when compared with placebo? A randomized controlled trial.
2010 Dec
Current approach in the diagnosis and management of panuveitis.
2010 Jan-Feb
Inhibitory effect of anticholinergics on the contraction of isolated caprine urinary bladder detrusor muscle.
2010 Jul
Acute postoperative endophthalmitis by Gemella haemolysans.
2010 May-Jun
Refractive error and visual functions in children with special needs compared with the first grade school students in oman.
2010 Oct
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Patents

Sample Use Guides

Adults and Adolescents 12 Years of Age and Older: 1 tablet or 5 mL (1 teaspoonful) of the oral solution every 4 to 6 hours as needed; do not exceed 6 tablets or 30 mL (6 teaspoonfuls) in 24 hours. Children 6 to 11 Years of Age: 1/2 tablet or 2.5 mL (1/2 teaspoonful) of the oral solution every 4 to 6 hours as needed; do not exceed 3 tablets or 15 mL (3 teaspoonfuls) in 24 hours.
Route of Administration: Oral
Isolated caprine urinary bladder detrusor muscle strips were incubated with homatropine at 5 uM after being contracted with 100 mum acetylcholine. The drug inhibited the ACh-induced contraction of the caprine detrusor and that this inhibition was reversed by raising the concentration of ACh.
Name Type Language
HOMATROPINE HYDROBROMIDE
EP   MART.   MI   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
Common Name English
HOMATROPINE HYDROBROMIDE [WHO-IP]
Common Name English
HOMATROPINE HYDROBROMIDE [EP MONOGRAPH]
Common Name English
HOMATROPINE HYDROBROMIDE [VANDF]
Common Name English
HOMATROPINE HYDROBROMIDE [USP MONOGRAPH]
Common Name English
BENZENEACETIC ACID, .ALPHA.-HYDROXY-, 8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL ESTER, HYDROBROMIDE, ENDO-(±)-
Common Name English
HOMATROPINI HYDROBROMIDUM [WHO-IP LATIN]
Common Name English
BENZENEACETIC ACID, .ALPHA.-HYDROXY-, 8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL ESTER, HBR, ENDO-(±)-
Common Name English
HOMATROPINE HYDROBROMIDE [MART.]
Common Name English
Homatropine hydrobromide [WHO-DD]
Common Name English
HOMATROPINE HYDROBROMIDE [JAN]
Common Name English
HOMATROPINE HYDROBROMIDE [MI]
Common Name English
NSC-757047
Code English
HOMATROPINE HYDROBROMIDE [USP-RS]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29704
Created by admin on Fri Dec 15 15:12:04 GMT 2023 , Edited by admin on Fri Dec 15 15:12:04 GMT 2023
NCI_THESAURUS C29706
Created by admin on Fri Dec 15 15:12:04 GMT 2023 , Edited by admin on Fri Dec 15 15:12:04 GMT 2023
Code System Code Type Description
RXCUI
235428
Created by admin on Fri Dec 15 15:12:04 GMT 2023 , Edited by admin on Fri Dec 15 15:12:04 GMT 2023
PRIMARY RxNorm
EPA CompTox
DTXSID5045099
Created by admin on Fri Dec 15 15:12:04 GMT 2023 , Edited by admin on Fri Dec 15 15:12:04 GMT 2023
PRIMARY
SMS_ID
100000078129
Created by admin on Fri Dec 15 15:12:04 GMT 2023 , Edited by admin on Fri Dec 15 15:12:04 GMT 2023
PRIMARY
NSC
757047
Created by admin on Fri Dec 15 15:12:04 GMT 2023 , Edited by admin on Fri Dec 15 15:12:04 GMT 2023
PRIMARY
CAS
51-56-9
Created by admin on Fri Dec 15 15:12:04 GMT 2023 , Edited by admin on Fri Dec 15 15:12:04 GMT 2023
PRIMARY
MERCK INDEX
m6038
Created by admin on Fri Dec 15 15:12:04 GMT 2023 , Edited by admin on Fri Dec 15 15:12:04 GMT 2023
PRIMARY Merck Index
ChEMBL
CHEMBL1618018
Created by admin on Fri Dec 15 15:12:04 GMT 2023 , Edited by admin on Fri Dec 15 15:12:04 GMT 2023
PRIMARY
DAILYMED
BEW7469QZ0
Created by admin on Fri Dec 15 15:12:04 GMT 2023 , Edited by admin on Fri Dec 15 15:12:04 GMT 2023
PRIMARY
EVMPD
SUB14111MIG
Created by admin on Fri Dec 15 15:12:04 GMT 2023 , Edited by admin on Fri Dec 15 15:12:04 GMT 2023
PRIMARY
DRUG BANK
DBSALT001537
Created by admin on Fri Dec 15 15:12:04 GMT 2023 , Edited by admin on Fri Dec 15 15:12:04 GMT 2023
PRIMARY
RS_ITEM_NUM
1310008
Created by admin on Fri Dec 15 15:12:04 GMT 2023 , Edited by admin on Fri Dec 15 15:12:04 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
HOMATROPINE HYDROBROMIDE
Created by admin on Fri Dec 15 15:12:04 GMT 2023 , Edited by admin on Fri Dec 15 15:12:04 GMT 2023
PRIMARY Description: Colourless crystals or a white, crystalline powder; odourless. Solubility: Freely soluble in water; sparingly soluble in ethanol (~750 g/l) TS; practically insoluble in ether R. Category: Mydriatic. Storage: Homatropine hydrobromide should be kept in a tightly closed container, protected from light.Definition: Homatropine hydrobromide contains not less than 98.5% and not more than 101.0% of C16H21NO3,HBr, calculated with reference to the dried substance.
FDA UNII
BEW7469QZ0
Created by admin on Fri Dec 15 15:12:04 GMT 2023 , Edited by admin on Fri Dec 15 15:12:04 GMT 2023
PRIMARY
NCI_THESAURUS
C29093
Created by admin on Fri Dec 15 15:12:04 GMT 2023 , Edited by admin on Fri Dec 15 15:12:04 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-105-3
Created by admin on Fri Dec 15 15:12:04 GMT 2023 , Edited by admin on Fri Dec 15 15:12:04 GMT 2023
PRIMARY