HOMATROPINE

US Previously Marketed

First marketed in 1921

Details

Stereochemistry	EPIMERIC
Molecular Formula	C16H21NO3
Molecular Weight	275.3434
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

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

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 158 Target ID: CHEMBL2094109 Sources: http://downloads.lww.com/wolterskluwer_vitalstream_com/sample-content/9780781789134_Rosenfeld/samples/Chapter_02.pdf	Antagonist 2575

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cough 103 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/005213s038lbl.pdf	Palliative		Approved 8043	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

Title	Date	PubMed
Anticholinergic delirium caused by topical homatropine ophthalmologic solution: confirmation by anticholinergic radioreceptor assay in two cases.	1992 Spring	1627983
Buspirone, but not sumatriptan, induces miosis in humans: relevance for a serotoninergic pupil control.	1995 Mar	7697953
Scavenging of photogenerated oxidative species by antimuscarinic drugs: atropine and derivatives.	2002	12625946
Bilateral panuveitis in a child with hypohidrotic ectodermal dysplasia.	2002 Sep	12208261
Tubulointerstitial nephritis and uveitis syndrome.	2003 Apr	12703689
Microbial keratitis and vision loss with contact lenses.	2003 Jan	12772749
Characterizing the subjective, psychomotor, and physiological effects of a hydrocodone combination product (Hycodan) in non-drug-abusing volunteers.	2003 Jan	12404072
Structural basis of heroin and cocaine metabolism by a promiscuous human drug-processing enzyme.	2003 May	12679808
Corneal topographic changes following retinal surgery.	2004 Aug 3	15291963
Multifocal choroiditis--an unusual finding in Crohn's disease.	2004 Jul-Aug	15309983
Familial HLA-A2- and HLA-B7-associated anterior uveitis.	2004 Oct	15559654
Acute posterior multifocal placoid pigment epitheliopathy after meningococcal C conjugate vaccine.	2005 Apr	15807837
Dense membrane formation after combined phacoemulsification-trabeculectomy surgery.	2005 Jun	15932536
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	15841415
Evaluation of amniotic membrane transplantation as an adjunct to medical therapy as compared with medical therapy alone in acute ocular burns.	2005 Nov	16198422
Intramuscular ophthalmic homatropine vs. atropine to prevent lethality in rates with dichlorvos poisoning.	2006 Dec	18072136
Homatropine and psychosis in Weill-Marchesani syndrome.	2006 Jul	16832313
Efficacy of trypan blue in posterior capsulorhexis with optic capture in pediatric cataracts [ISRCTN48221688].	2006 Mar 16	16539738
[Neurotoxic effects induced by the topical administration of cycloplegics. A case report and review of the literature].	2006 Nov 16-30	17099852
Role of the medial prefrontal cortex in cardiovascular responses to acute restraint in rats.	2006 Nov 17	16938408
Pretreating rats with parenteral ophthalmic antimuscarinic agents decreases mortality from lethal organophosphate poisoning.	2007 Apr	17296800
Enantioseparation of chiral tropa alkaloids by means of cyclodextrin-modified microemulsion electrokinetic chromatography.	2007 Aug	17592616
Increasing the scale of true moving bed electrophoretic separations using filtration to reduce solvent volumetric flows between sections II and III.	2007 Jan 5	17097668
True moving bed electrophoresis using stepped electric field gradients.	2007 May	17492725
An "epidemic" of post cataract surgery endophthalmitis by a new organism.	2007 Nov-Dec	17951908
Metoclopramide protection of diazinon-induced toxicosis in chickens.	2007 Sep	17679771
Acute retinal necrosis complicating chickenpox in a healthy adult--a case report and review of literature.	2007 Spring	17984490
Capillary electrophoresis of tropane alkaloids and glycoalkaloids occurring in Solanaceae plants.	2008	18392571
Granuloma annulare anterior uveitis.	2008 Jan-Feb	18379945
Hypotony maculopathy in a patient with HLA-B27-associated uveitis.	2008 May-Jun	18569798
Voriconazole for the treatment of refractory Aspergillus fumigatus keratitis.	2008 May-Jun	18417831
First aid for complications of infectious keratitis.	2008 May-Jun	18417823
Managing corneal disease: focus on suppurative keratitis.	2009 Dec	20212926
Syphilitic palmoplantar keratoderma and ocular disease: a rare combination in an HIV-positive patient.	2009 Dec	20166572
Two differing presentations of chronic bilateral anterior uveitis.	2009 Feb	19187894
Peripheral ulcerative keratitis with bilateral optic nerve involvement as an initial presentation of acute lymphocytic leukemia in an adult.	2009 Feb	18008055
Keratouveitis caused by Euphorbia plant sap.	2009 Jul-Aug	19574703
Role of the bed nucleus of the stria terminalis in the cardiovascular responses to acute restraint stress in rats.	2009 May	18850495
Adverse drug effects in hospitalized elderly: data from the healthcare cost and utilization project.	2010	22291486
Tubulointerstitial nephritis with uveitis syndrome: A case report and review of literature.	2010 Apr	20835328
Is homatropine 5% effective in reducing pain associated with corneal abrasion when compared with placebo? A randomized controlled trial.	2010 Dec	21143399
LC-ESI MS/MS quantification of atropine and six other antimuscarinic tropane alkaloids in plasma.	2010 Jan	19855962
Current approach in the diagnosis and management of panuveitis.	2010 Jan-Feb	20029145
Inhibitory effect of anticholinergics on the contraction of isolated caprine urinary bladder detrusor muscle.	2010 Jul	20085574
The endogenous cannabinoid, anandamide, inhibits dopamine transporter function by a receptor-independent mechanism.	2010 Mar	20050977
Acute postoperative endophthalmitis by Gemella haemolysans.	2010 May-Jun	20413936
Refractive error and visual functions in children with special needs compared with the first grade school students in oman.	2010 Oct	21180428
Homocysteinethiolactone and paraoxonase: novel markers of diabetic retinopathy.	2010 Sep	20551012
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011 Jul 14	21599003
Efficacy assessment of various anticholinergic agents against topical sarin-induced miosis and visual impairment in rats.	2012 Apr	22247005

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.

Name

Type

Language

HOMATROPINE

Common Name

English

HOMATROPINE METHYLBROMIDE IMPURITY B [EP]

Common Name

English

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

Common Name

English

HOMATROPINE HYDROBROMIDE IMPURITY A [EP]

Common Name

English

HOMATROPINE [MART.]

Common Name

English

HOMATROPINE [MI]

Common Name

English

HOMATROPINE [VANDF]

Common Name

English

HOMATROPINE [WHO-DD]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000000104