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

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 160 Target ID: CHEMBL2094109 Sources: http://downloads.lww.com/wolterskluwer_vitalstream_com/sample-content/9780781789134_Rosenfeld/samples/Chapter_02.pdf	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cough 106 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/005213s038lbl.pdf	Palliative		Approved 8429	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
Anticholinergic delirium caused by topical homatropine ophthalmologic solution: confirmation by anticholinergic radioreceptor assay in two cases.	1992 Spring	1627983
Bilateral panuveitis in a child with hypohidrotic ectodermal dysplasia.	2002 Sep	12208261
Characterizing the subjective, psychomotor, and physiological effects of a hydrocodone combination product (Hycodan) in non-drug-abusing volunteers.	2003 Jan	12404072
Corneal topographic changes following retinal surgery.	2004 Aug 3	15291963
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
Syphilitic palmoplantar keratoderma and ocular disease: a rare combination in an HIV-positive patient.	2009 Dec	20166572
Peripheral ulcerative keratitis with bilateral optic nerve involvement as an initial presentation of acute lymphocytic leukemia in an adult.	2009 Feb	18008055
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
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
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

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

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

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