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Details

Stereochemistry EPIMERIC
Molecular Formula C16H21NO3.BrH
Molecular Weight 356.2549
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HOMATROPINE HYDROBROMIDE

SMILES

CN1[C@@]2([H])CC[C@]1([H])C[C@@]([H])(C2)OC(=O)C([H])(c3ccccc3)O.Br

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

Molecular Formula BrH
Molecular Weight 80.9115
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C16H21NO3
Molecular Weight 275.3434
Charge 0
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 2 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

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

4.15497585E11
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
Scavenging of photogenerated oxidative species by antimuscarinic drugs: atropine and derivatives.
2002
Tubulointerstitial nephritis and uveitis syndrome.
2003 Apr
Microbial keratitis and vision loss with contact lenses.
2003 Jan
Characterizing the subjective, psychomotor, and physiological effects of a hydrocodone combination product (Hycodan) in non-drug-abusing volunteers.
2003 Jan
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
Multifocal choroiditis--an unusual finding in Crohn's disease.
2004 Jul-Aug
Familial HLA-A2- and HLA-B7-associated anterior uveitis.
2004 Oct
Acute posterior multifocal placoid pigment epitheliopathy after meningococcal C conjugate vaccine.
2005 Apr
Dense membrane formation after combined phacoemulsification-trabeculectomy surgery.
2005 Jun
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
Intramuscular ophthalmic homatropine vs. atropine to prevent lethality in rates with dichlorvos poisoning.
2006 Dec
Homatropine and psychosis in Weill-Marchesani syndrome.
2006 Jul
Efficacy of trypan blue in posterior capsulorhexis with optic capture in pediatric cataracts [ISRCTN48221688].
2006 Mar 16
[Neurotoxic effects induced by the topical administration of cycloplegics. A case report and review of the literature].
2006 Nov 16-30
Role of the medial prefrontal cortex in cardiovascular responses to acute restraint in rats.
2006 Nov 17
Pretreating rats with parenteral ophthalmic antimuscarinic agents decreases mortality from lethal organophosphate poisoning.
2007 Apr
Enantioseparation of chiral tropa alkaloids by means of cyclodextrin-modified microemulsion electrokinetic chromatography.
2007 Aug
Increasing the scale of true moving bed electrophoretic separations using filtration to reduce solvent volumetric flows between sections II and III.
2007 Jan 5
True moving bed electrophoresis using stepped electric field gradients.
2007 May
An "epidemic" of post cataract surgery endophthalmitis by a new organism.
2007 Nov-Dec
Metoclopramide protection of diazinon-induced toxicosis in chickens.
2007 Sep
Acute retinal necrosis complicating chickenpox in a healthy adult--a case report and review of literature.
2007 Spring
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
First aid for complications of infectious keratitis.
2008 May-Jun
Managing corneal disease: focus on suppurative keratitis.
2009 Dec
Syphilitic palmoplantar keratoderma and ocular disease: a rare combination in an HIV-positive patient.
2009 Dec
Two differing presentations of chronic bilateral anterior uveitis.
2009 Feb
Peripheral ulcerative keratitis with bilateral optic nerve involvement as an initial presentation of acute lymphocytic leukemia in an adult.
2009 Feb
Keratouveitis caused by Euphorbia plant sap.
2009 Jul-Aug
Role of the bed nucleus of the stria terminalis in the cardiovascular responses to acute restraint stress in rats.
2009 May
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
LC-ESI MS/MS quantification of atropine and six other antimuscarinic tropane alkaloids in plasma.
2010 Jan
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
The endogenous cannabinoid, anandamide, inhibits dopamine transporter function by a receptor-independent mechanism.
2010 Mar
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
Homocysteinethiolactone and paraoxonase: novel markers of diabetic retinopathy.
2010 Sep
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Efficacy assessment of various anticholinergic agents against topical sarin-induced miosis and visual impairment in rats.
2012 Apr
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.
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:10:12 UTC 2021
Edited
by admin
on Fri Jun 25 21:10:12 UTC 2021
Record UNII
BEW7469QZ0
Record Status Validated (UNII)
Record Version
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Name Type Language
HOMATROPINE HYDROBROMIDE
EP   MART.   MI   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
Common Name English
HOMATROPINE HYDROBROMIDE [USP]
Common Name English
HOMATROPINE HYDROBROMIDE [WHO-IP]
Common Name English
HOMATROPINE HYDROBROMIDE [EP MONOGRAPH]
Common Name English
HOMATROPINE HYDROBROMIDE [VANDF]
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 [MI]
Common Name English
NSC-757047
Code English
HOMATROPINE HYDROBROMIDE [WHO-DD]
Common Name English
HOMATROPINE HYDROBROMIDE [USP-RS]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29704
Created by admin on Fri Jun 25 21:10:12 UTC 2021 , Edited by admin on Fri Jun 25 21:10:12 UTC 2021
NCI_THESAURUS C29706
Created by admin on Fri Jun 25 21:10:12 UTC 2021 , Edited by admin on Fri Jun 25 21:10:12 UTC 2021
Code System Code Type Description
RXCUI
235428
Created by admin on Fri Jun 25 21:10:12 UTC 2021 , Edited by admin on Fri Jun 25 21:10:12 UTC 2021
PRIMARY RxNorm
EPA CompTox
51-56-9
Created by admin on Fri Jun 25 21:10:12 UTC 2021 , Edited by admin on Fri Jun 25 21:10:12 UTC 2021
PRIMARY
CAS
51-56-9
Created by admin on Fri Jun 25 21:10:12 UTC 2021 , Edited by admin on Fri Jun 25 21:10:12 UTC 2021
PRIMARY
MERCK INDEX
M6038
Created by admin on Fri Jun 25 21:10:12 UTC 2021 , Edited by admin on Fri Jun 25 21:10:12 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL1618018
Created by admin on Fri Jun 25 21:10:12 UTC 2021 , Edited by admin on Fri Jun 25 21:10:12 UTC 2021
PRIMARY
EVMPD
SUB14111MIG
Created by admin on Fri Jun 25 21:10:12 UTC 2021 , Edited by admin on Fri Jun 25 21:10:12 UTC 2021
PRIMARY
USP_CATALOG
1310008
Created by admin on Fri Jun 25 21:10:12 UTC 2021 , Edited by admin on Fri Jun 25 21:10:12 UTC 2021
PRIMARY USP-RS
DRUG BANK
DBSALT001537
Created by admin on Fri Jun 25 21:10:12 UTC 2021 , Edited by admin on Fri Jun 25 21:10:12 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
HOMATROPINE HYDROBROMIDE
Created by admin on Fri Jun 25 21:10:12 UTC 2021 , Edited by admin on Fri Jun 25 21:10:12 UTC 2021
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 Jun 25 21:10:12 UTC 2021 , Edited by admin on Fri Jun 25 21:10:12 UTC 2021
PRIMARY
NCI_THESAURUS
C29093
Created by admin on Fri Jun 25 21:10:12 UTC 2021 , Edited by admin on Fri Jun 25 21:10:12 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-105-3
Created by admin on Fri Jun 25 21:10:12 UTC 2021 , Edited by admin on Fri Jun 25 21:10:12 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
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IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
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ACTIVE MOIETY