DEPTROPINE CITRATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H27NO.C6H8O7
Molecular Weight	525.5901
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)CC(O)(CC(O)=O)C(O)=O.CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC3C4=C(CCC5=C3C=CC=C5)C=CC=C4

InChI

InChIKey=CHQGYMXXKZPWOI-BWSPSPBFSA-N

InChI=1S/C23H27NO.C6H8O7/c1-24-18-12-13-19(24)15-20(14-18)25-23-21-8-4-2-6-16(21)10-11-17-7-3-5-9-22(17)23;7-3(8)1-6(13,5(11)12)2-4(9)10/h2-9,18-20,23H,10-15H2,1H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/t18-,19+,20+;

HIDE SMILES / InChI

Molecular Formula	C6H8O7
Molecular Weight	192.1235
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C23H27NO
Molecular Weight	333.4666
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27894093 | https://www.ncbi.nlm.nih.gov/pubmed/11145097

Deptropine citrate is a well-known H1-histamine receptor antagonist and muscarinic receptor antagonist. It is prescribed frequently for treatment of asthma, although there has been a sharp decrease in prescriptions since 1994. Deptropine is gradually being replaced by inhaled beta 2 adrenergic agonists and glucocorticosteroids as the preferred clinical prescription. Recently deptropine has garnered interest as a potential treatment for breast cancer. In vitro studies have shown deptropine citrate has inhibitory effects on cell viability and mammosphere formation in Breast Cancer Stem Cells (BCSCs). However, it does not seem to inhibit the self-renewal capacity of the breast cancer cell line MDA-MB-231 when it is enriched with Cancer Stem Cells.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 315 Target ID: P35367 Gene ID: 3269.0 Gene Symbol: HRH1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27894093	Antagonist 2778
Muscarinic acetylcholine receptor 160 Target ID: CHEMBL2094109 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27894093	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Asthma 241 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11145097	Primary		Not Provided 504	Unknown Approved Use Unknown
Breast cancer 434 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27894093	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Anti-asthmatic drugs and dosage forms in children: a cross-sectional study.	2002 Aug	12227250
Computed critiquing integrated into daily clinical practice affects physicians' behavior--a randomized clinical trial with AsthmaCritic.	2006	16964364

Sample Use Guides

In Vivo Use Guide

aerosolized: 0.2 mg daily oral: 0.2 mg daily

Route of Administration: Other

In Vitro Use Guide

The ability to form mammospheres is correlated with the frequency of Cancer stem cells (CSCs) and progenitor cells in tumor cell lines. Thus, was analyzed the effects of different concentrations of deptropine citrate on mammosphere formation of MDA-MB-231 and 4T1-luc2 cells. In MDA-MB-231 cells, deptropine citrate reduced the size as well as the number of mammospheres significantly in a dose-dependent manner. The IC50 values of deptropine citrate for MDA-MB-231 spheres were 5 μM.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:50:43 UTC 2023` Edited by `admin` on `Fri Dec 15 16:50:43 UTC 2023`
Record UNII	05LW13XKKR
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DEPTROPINE CITRATE

Common Name

English

DEPTROPINE CITRATE [EP IMPURITY]

Common Name

English

DIBENZHEPTROPINE CITRATE

Common Name

English

3-(10,11-DIHYDRO-5H-DIBENZO(A,D)CYCLOHEPTEN-5-YLOXY)TROPANE CITRATE

Common Name

English

TROPANE, 3.ALPHA.-((10,11-DIHYDRO-5H-DIBENZO(A,D)CYCLOHEPTEN-5-YL)OXY)-, CITRATE (1:1)

Common Name

English

DEPTROPINE CITRATE [MI]

Common Name

English

1.ALPHA.H,5.ALPHA.H-TROPANE, 3.ALPHA.-((10,11-DIHYDRO-5H-DIBENZO(A,D)CYCLOHEPTEN-5-YL)OXY)-, CITRATE (1:1)

Common Name

English

DEPTROPINE CITRATE [EP MONOGRAPH]

Common Name

English

BRONTINE

Brand Name

English

DEPTROPINE CITRATE [MART.]

Common Name

English

BS 6987

Code

English

NSC-169431

Code

English

DEPTROPINE DIHYDROGEN CITRATE

Common Name

English

BS-6987

Code

English

Deptropine citrate [WHO-DD]

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID4045557