HOMATROPINE

US Unapproved Medicine

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 73 Target ID: CHEMBL2094109 Sources: http://downloads.lww.com/wolterskluwer_vitalstream_com/sample-content/9780781789134_Rosenfeld/samples/Chapter_02.pdf	Antagonist 1131

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cough 48 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/005213s038lbl.pdf	Palliative		Approved 4033	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
Herpes simplex virus type 1 associated acute retinal necrosis following encephalitis.	2001	11756904
Tris(2,2'-bipyridine)ruthenium(II) electrogenerated chemiluminescence of alkaloid type drugs with solid phase extraction sample preparation.	2001 Jan	11205508
[Neurological manifestations in the intoxication of infants by dimethicone combined with homatropine: report of 6 cases].	2001 Jun	11400033
Contact allergy to atropine and other mydriatic agents in eye drops.	2001 Nov	11722501
Scavenging of photogenerated oxidative species by antimuscarinic drugs: atropine and derivatives.	2002	12625946
[Effect of pilocarpine and cycloplegic substances on ophthalmic tone in healthy eyes and ones with glaucoma].	2002 Jan-Feb	11898357
Topical ketorolac tromethamine 0.5% versus diclofenac sodium 0.1% to inhibit miosis during cataract surgery.	2002 Mar	11973101
Bilateral panuveitis in a child with hypohidrotic ectodermal dysplasia.	2002 Sep	12208261
Human carboxylesterase 1: from drug metabolism to drug discovery.	2003 Jun	12773168
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
Dense membrane formation after combined phacoemulsification-trabeculectomy surgery.	2005 Jun	15932536
Evaluation of amniotic membrane transplantation as an adjunct to medical therapy as compared with medical therapy alone in acute ocular burns.	2005 Nov	16198422
Homatropine and psychosis in Weill-Marchesani syndrome.	2006 Jul	16832313
Role of the medial prefrontal cortex in cardiovascular responses to acute restraint in rats.	2006 Nov 17	16938408
Enantioseparation of chiral tropa alkaloids by means of cyclodextrin-modified microemulsion electrokinetic chromatography.	2007 Aug	17592616
Acute retinal necrosis complicating chickenpox in a healthy adult--a case report and review of literature.	2007 Spring	17984490
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
Peripheral ulcerative keratitis with bilateral optic nerve involvement as an initial presentation of acute lymphocytic leukemia in an adult.	2009 Feb	18008055
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
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