HOMATROPINE

US Previously Marketed

First marketed in 1921

Details

Stereochemistry	EPIMERIC
Molecular Formula	C16H21NO3
Molecular Weight	275.3428
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=ZTVIKZXZYLEVOL-MCOXGKPRSA-N

InChI=1S/C16H21NO3/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/t12-,13+,14+,15?

HIDE SMILES / InChI

Molecular Formula	C16H21NO3
Molecular Weight	275.3428
Charge	0
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	3 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/005213s038lbl.pdf

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.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Muscarinic acetylcholine receptor 162 Target ID: CHEMBL2094109 Sources: http://downloads.lww.com/wolterskluwer_vitalstream_com/sample-content/9780781789134_Rosenfeld/samples/Chapter_02.pdf	Antagonist 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cough 106 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/005213s038lbl.pdf	Palliative		Approved 8583	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

Title	Date	PubMed
Efficacy assessment of various anticholinergic agents against topical sarin-induced miosis and visual impairment in rats.	2012-04	22247005
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011-07-14	21599003
Is homatropine 5% effective in reducing pain associated with corneal abrasion when compared with placebo? A randomized controlled trial.	2010-12	21143399
Refractive error and visual functions in children with special needs compared with the first grade school students in oman.	2010-10	21180428
Homocysteinethiolactone and paraoxonase: novel markers of diabetic retinopathy.	2010-09	20551012
Inhibitory effect of anticholinergics on the contraction of isolated caprine urinary bladder detrusor muscle.	2010-07	20085574
Acute postoperative endophthalmitis by Gemella haemolysans.	2010-04-24	20413936
Tubulointerstitial nephritis with uveitis syndrome: A case report and review of literature.	2010-04	20835328
The endogenous cannabinoid, anandamide, inhibits dopamine transporter function by a receptor-independent mechanism.	2010-03	20050977
LC-ESI MS/MS quantification of atropine and six other antimuscarinic tropane alkaloids in plasma.	2010-01	19855962
Adverse drug effects in hospitalized elderly: data from the healthcare cost and utilization project.	2010	22291486
Current approach in the diagnosis and management of panuveitis.	2009-12-24	20029145
Managing corneal disease: focus on suppurative keratitis.	2009-12	20212926
Syphilitic palmoplantar keratoderma and ocular disease: a rare combination in an HIV-positive patient.	2009-12	20166572
Keratouveitis caused by Euphorbia plant sap.	2009-07-04	19574703
Role of the bed nucleus of the stria terminalis in the cardiovascular responses to acute restraint stress in rats.	2009-05	18850495
Two differing presentations of chronic bilateral anterior uveitis.	2009-02	19187894
Peripheral ulcerative keratitis with bilateral optic nerve involvement as an initial presentation of acute lymphocytic leukemia in an adult.	2009-02	18008055
Hypotony maculopathy in a patient with HLA-B27-associated uveitis.	2008-06-24	18569798
Voriconazole for the treatment of refractory Aspergillus fumigatus keratitis.	2008-04-18	18417831
First aid for complications of infectious keratitis.	2008-04-18	18417823
Granuloma annulare anterior uveitis.	2008-04-02	18379945
Capillary electrophoresis of tropane alkaloids and glycoalkaloids occurring in Solanaceae plants.	2008	18392571
An "epidemic" of post cataract surgery endophthalmitis by a new organism.	2007-10-24	17951908
Metoclopramide protection of diazinon-induced toxicosis in chickens.	2007-09	17679771
Enantioseparation of chiral tropa alkaloids by means of cyclodextrin-modified microemulsion electrokinetic chromatography.	2007-08	17592616
True moving bed electrophoresis using stepped electric field gradients.	2007-05	17492725
Pretreating rats with parenteral ophthalmic antimuscarinic agents decreases mortality from lethal organophosphate poisoning.	2007-04	17296800
Increasing the scale of true moving bed electrophoretic separations using filtration to reduce solvent volumetric flows between sections II and III.	2007-01-05	17097668
Acute retinal necrosis complicating chickenpox in a healthy adult--a case report and review of literature.	2007	17984490
Intramuscular ophthalmic homatropine vs. atropine to prevent lethality in rates with dichlorvos poisoning.	2006-12	18072136
Role of the medial prefrontal cortex in cardiovascular responses to acute restraint in rats.	2006-11-17	16938408
[Neurotoxic effects induced by the topical administration of cycloplegics. A case report and review of the literature].	2006-11-14	17099852
Homatropine and psychosis in Weill-Marchesani syndrome.	2006-07	16832313
Efficacy of trypan blue in posterior capsulorhexis with optic capture in pediatric cataracts [ISRCTN48221688].	2006-03-16	16539738
Evaluation of amniotic membrane transplantation as an adjunct to medical therapy as compared with medical therapy alone in acute ocular burns.	2005-11	16198422
Dense membrane formation after combined phacoemulsification-trabeculectomy surgery.	2005-06	15932536
Acute posterior multifocal placoid pigment epitheliopathy after meningococcal C conjugate vaccine.	2005-04	15807837
Frontotemporal dementia with co-occurrence of astrocytic plaques and tufted astrocytes, and severe degeneration of the cerebral white matter: a variant of corticobasal degeneration?	2005-03	15841415
Familial HLA-A2- and HLA-B7-associated anterior uveitis.	2004-10	15559654
Multifocal choroiditis--an unusual finding in Crohn's disease.	2004-08-18	15309983
Corneal topographic changes following retinal surgery.	2004-08-03	15291963
Human carboxylesterase 1: from drug metabolism to drug discovery.	2003-06	12773168
Structural basis of heroin and cocaine metabolism by a promiscuous human drug-processing enzyme.	2003-05	12679808
Tubulointerstitial nephritis and uveitis syndrome.	2003-04	12703689
Microbial keratitis and vision loss with contact lenses.	2003-01	12772749
Characterizing the subjective, psychomotor, and physiological effects of a hydrocodone combination product (Hycodan) in non-drug-abusing volunteers.	2003-01	12404072
Scavenging of photogenerated oxidative species by antimuscarinic drugs: atropine and derivatives.	2002	12625946
Buspirone, but not sumatriptan, induces miosis in humans: relevance for a serotoninergic pupil control.	1995-03	7697953
Anticholinergic delirium caused by topical homatropine ophthalmologic solution: confirmation by anticholinergic radioreceptor assay in two cases.	1992	1627983

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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 `Mon Mar 31 18:47:55 GMT 2025` Edited by `admin` on `Mon Mar 31 18:47:55 GMT 2025`
Record UNII	8QS6WCL55Z
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BENZENEACETIC ACID, .ALPHA.-HYDROXY-, 8-METHYL-8-AZABICYCLO(.2.1)OCT-3-YL ESTER

Preferred Name

English

HOMATROPINE

Common Name

English

HOMATROPINE METHYLBROMIDE IMPURITY B [EP IMPURITY]

Common Name

English

HOMATROPINE [MART.]

Common Name

English

HOMATROPINE [MI]

Common Name

English

HOMATROPINE [VANDF]

Common Name

English

Homatropine [WHO-DD]

Common Name

English

HOMATROPINE HYDROBROMIDE IMPURITY A [EP IMPURITY]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000000104