IODODOXORUBICIN HYDROCHLORIDE

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H28INO10.ClH
Molecular Weight	689.877
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of IODODOXORUBICIN HYDROCHLORIDE

Structure Search

SMILES

Cl.[H][C@@]1(C[C@H](N)[C@H](I)[C@H](C)O1)O[C@H]2C[C@@](O)(CC3=C(O)C4=C(C(=O)C5=C(OC)C=CC=C5C4=O)C(O)=C23)C(=O)CO

InChI

InChIKey=RIXHOXYAFWQBGU-RUELKSSGSA-N

InChI=1S/C27H28INO10.ClH/c1-10-22(28)13(29)6-17(38-10)39-15-8-27(36,16(31)9-30)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34;/h3-5,10,13,15,17,22,30,33,35-36H,6-9,29H2,1-2H3;1H/t10-,13-,15-,17-,22+,27-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

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

Molecular Formula	C27H28INO10
Molecular Weight	653.4164
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8142261 | https://www.ncbi.nlm.nih.gov/pubmed/7501474

Iododoxorubicin is an anthracycline derivative patented by Farmitalia Carlo Erba S.p.A. for cancer treatment. In preclinical studies, Iododoxorubicin has demonstrated significantly reduced levels of cardiotoxicity compared to anthracyclines. Unfortunately, during phase II clinical trials Iododoxorubicin failed to demonstrate efficacy in an advanced breast cancer patient

Originator

Approval Year

PubMed

Title	Date	PubMed
Chemical and biological characterization of 4'-iodo-4'-deoxydoxorubicin.	1987 Aug 1	3607745
Phase II study of 4'-iodo-4'-deoxydoxorubicin in non-resectable non-small-cell lung cancer.	1993	8393388
Current therapeutic possibilities in primary and secondary amyloidosis and our experience with 31 patients.	2003 Jul	12817067
AL amyloidosis with renal involvement.	2007	17851224
[Advances in diagnosis and treatment of AL amyloidosis].	2008 Apr	18634370
Antihypertensive drug guanabenz is active in vivo against both yeast and mammalian prions.	2008 Apr 23	18431471
A camelid anti-PrP antibody abrogates PrP replication in prion-permissive neuroblastoma cell lines.	2010 Mar 22	20339552

Patents

Sample Use Guides

In Vivo Use Guide

80 mg m-2 i.v. was given 3 weekly for a maximum of six cycles

Route of Administration: Intravenous

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:51:54 GMT 2023` Edited by `admin` on `Fri Dec 15 15:51:54 GMT 2023`
Record UNII	31I1O326SE
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

IODODOXORUBICIN HYDROCHLORIDE

Common Name

English

IODODOXORUBICIN HCL

Common Name

English

5,12-NAPHTHACENEDIONE, 10-(((2R,4S,5S,6S)-4-AMINOTETRAHYDRO-5-IODO-6-METHYL-2H-PYRAN-2-YL)OXY)-7,8,9,10-TETRAHYDRO-6,8,11-TRIHYDROXY-8-(HYDROXYACETYL)-1-METHOXY-, HYDROCHLORIDE, (8S,10S)-

Systematic Name

English

4'-IODO-4'-DEOXYDOXORUBICIN HYDROCHLORIDE

Common Name

English

NSC-378901

Code

English

Code System Code Type Description

NSC

378901