CIPAMFYLLINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H17N5O2
Molecular Weight	275.3064
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=NC2=C(N1)N(CC3CC3)C(=O)N(CC4CC4)C2=O

InChI

InChIKey=KSPYMJJKQMWWNB-UHFFFAOYSA-N

InChI=1S/C13H17N5O2/c14-12-15-9-10(16-12)17(5-7-1-2-7)13(20)18(11(9)19)6-8-3-4-8/h7-8H,1-6H2,(H3,14,15,16)

HIDE SMILES / InChI

Molecular Formula	C13H17N5O2
Molecular Weight	275.3064
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17352685
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/12174103 | https://www.ncbi.nlm.nih.gov/pubmed/21456625 | http://adisinsight.springer.com/drugs/800004678

Cipamfylline is a xanthine, a theophylline analogue, and is a potent and selective inhibitor of phosphodiesterase type 4 (PDE-4). Cipamfylline was tested in patients with a diagnosis of atopic dermatitis and in two human models of acute and chronic irritant contact dermatitis. The outcome of the study revealed that cipamfylline was more effective than vehicle in treating atopic dermatitis, but less effective than a group II steroid, hydrocortisone-17-butyrate both in the treatment of atopic dermatitis and irritant contact dermatitis. The absorption of cipamfylline and the subsequent systemic exposure might be the reason why further clinical studies with higher doses of cipamfylline have not been published.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Phosphodiesterase 4A 13 Target ID: CHEMBL254 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21456625	Inhibitor 8297		1.6 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Atopic dermatitis 43 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12174103	Primary		Phase II 1132	Unknown Approved Use Unknown
Irritant contact dermatitis 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12709818	Primary		Phase II 1132	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
0.15 % 1 times / day multiple, topical Studied dose Dose: 0.15 %, 1 times / day Route: topical Route: multiple Dose: 0.15 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12174103 Page: p.305	unhealthy, ADULT n = 54 Health Status: unhealthy Condition: atopic dermatitis Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 54 Sources: https://pubmed.ncbi.nlm.nih.gov/12174103 Page: p.305	Sources: https://pubmed.ncbi.nlm.nih.gov/12174103 Page: p.305

Sourcing

Vendor/Aggregator	ID	URL
Alfa Chemistry	ACM132210436	http://www.alfa-chemistry.com/search.aspx?q=ACM132210436
Compound Cloud	71356
MuseChem	M116901	https://www.musechem.com/product/M116901.html
Tetrahedron	TS31040	http://www.thsci.com/search.do?q=TS31040

PubMed

Title	Date	PubMed
Theoretical and experimental investigations on the morphology of pharmaceutical crystals.	2002 Jul	12115826
Gateways to clinical trials.	2003 Apr	12743628
The effect of the PDE-4 inhibitor (cipamfylline) in two human models of irritant contact dermatitis.	2003 Apr	12709818
Gateways to clinical trials.	2003 May	12808477
Highly selective phosphodiesterase 4 inhibitors for the treatment of allergic skin diseases and psoriasis.	2007 Mar	17352685

Patents

Sample Use Guides

In Vivo Use Guide

0.15% cream applied twice daily with a maximum application of 2 g per day

Route of Administration: Topical

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:53:56 GMT 2023` Edited by `admin` on `Fri Dec 15 15:53:56 GMT 2023`
Record UNII	AFP56R140L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CIPAMFYLLINE

Official Name

English

1H-PURINE-2,6-DIONE, 8-AMINO-1,3-BIS(CYCLOPROPYLMETHYL)-3,7-DIHYDRO-

Systematic Name

English

CIPAMFYLLINE [USAN]

Common Name

English

8-Amino-1,3-bis(cyclopropylmethyl)xanthine

Systematic Name

English

cipamfylline [INN]

Common Name

English

BRL-61063

Code

English

BRL61063

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C744