PEPLOMYCIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C61H88N18O21S2
Molecular Weight	1473.589
Optical Activity	UNSPECIFIED
Defined Stereocenters	20 / 20
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]7(O[C@@H]1[C@H](O[C@H]([C@H](NC(=O)C2=NC(=NC(N)=C2C)[C@H](CC(N)=O)NC[C@H](N)C(N)=O)C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCCC3=NC(=CS3)C4=NC(=CS4)C(=O)NCCCN[C@@H](C)C5=CC=CC=C5)C6=CN=CN6)O[C@@H](CO)[C@@H](O)[C@@H]1O)O[C@H](CO)[C@@H](O)[C@H](OC(N)=O)[C@@H]7O

InChI

InChIKey=QIMGFXOHTOXMQP-GFAGFCTOSA-N

InChI=1S/C61H88N18O21S2/c1-24-39(76-52(79-50(24)64)31(16-37(63)83)71-17-30(62)51(65)89)56(93)78-41(47(32-18-67-23-72-32)98-60-49(45(87)43(85)35(19-80)97-60)99-59-46(88)48(100-61(66)95)44(86)36(20-81)96-59)57(94)73-27(4)42(84)25(2)53(90)77-40(28(5)82)55(92)70-15-12-38-74-34(22-101-38)58-75-33(21-102-58)54(91)69-14-9-13-68-26(3)29-10-7-6-8-11-29/h6-8,10-11,18,21-23,25-28,30-31,35-36,40-49,59-60,68,71,80-82,84-88H,9,12-17,19-20,62H2,1-5H3,(H2,63,83)(H2,65,89)(H2,66,95)(H,67,72)(H,69,91)(H,70,92)(H,73,94)(H,77,90)(H,78,93)(H2,64,76,79)/t25-,26-,27+,28+,30-,31-,35-,36+,40-,41-,42-,43+,44+,45-,46-,47-,48-,49-,59+,60-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C61H88N18O21S2
Molecular Weight	1473.589
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	20 / 20
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.anticancer-drug.net/antibiotic/peplomycin.htm
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/83987 | http://www.rad-ar.or.jp/siori/kekka.cgi?n=39236

Peplomycin has been developed as novel analog of bleomycin, which has less pulmonary toxicity than bleomycin. Peplomycin has been the subject of extensive studies in Japan and Europe. It is indicated for the treatment of malignant lymphoma, head and neck cancer, lung cancer, prostate cancer and skin cancer. General side effects are: digestive symptoms such as stomatitis, anorexia, nausea/vomiting, general malaise, depilation, fever, chills etc.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Synthesis of DNA 4 Target ID: WP1925 Sources: http://www.anticancer-drug.net/antibiotic/peplomycin.htm \| https://www.ncbi.nlm.nih.gov/pubmed/83987	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Prostate cancer 178 Sources: http://www.rad-ar.or.jp/siori/kekka.cgi?n=39236	Primary	Approved 8429	Pepleo Approved Use It is used for the treatment of skin cancer, head and neck malignancy, lung cancer, prostate cancer, malignant lymphoma
Lung cancer 69 Sources: http://www.rad-ar.or.jp/siori/kekka.cgi?n=39236	Primary	Approved 8429	Pepleo Approved Use It is used for the treatment of skin cancer, head and neck malignancy, lung cancer, prostate cancer, malignant lymphoma
Malignant lymphoma 10 Sources: http://www.rad-ar.or.jp/siori/kekka.cgi?n=39236	Primary	Approved 8429	Pepleo Approved Use It is used for the treatment of skin cancer, head and neck malignancy, lung cancer, prostate cancer, malignant lymphoma
Skin cancer 23 Sources: http://www.rad-ar.or.jp/siori/kekka.cgi?n=39236	Primary	Approved 8429	Pepleo Approved Use It is used for the treatment of skin cancer, head and neck malignancy, lung cancer, prostate cancer, malignant lymphoma
Head and neck cancer 50 Sources: http://www.rad-ar.or.jp/siori/kekka.cgi?n=39236	Primary	Approved 8429	Pepleo Approved Use It is used for the treatment of skin cancer, head and neck malignancy, lung cancer, prostate cancer, malignant lymphoma

PubMed

Title	Date	PubMed
Biological studies on the degradation products of 3-[(S)-1'-phenylethylamino]propylaminobleomycin: a novel analog (pepleomycin).	1979 Jan	83987
A review of clinical studies of pepleomycin.	1980	6160600
Effect of pepleomycin in prostatic cancer. A preliminary report.	1980	6163206

Patents

Sample Use Guides

In Vivo Use Guide

3.2 mg/m2 once a day, 2-3 times per week (22.4 mg/m2 per week)

Route of Administration: Other

In Vitro Use Guide

Peplomycin showed the following antimicrobial potency against Mycobacterium smegmatis ATCC 607 – 873 ug potency/mg and gave the following very correlative result on the growth inhibition of cultured HeLa S3 cells – ID50 = 0.84 ug/ml.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:38:51 GMT 2023` Edited by `admin` on `Fri Dec 15 18:38:51 GMT 2023`
Record UNII	56H9L80NIZ
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

PEPLOMYCIN

Official Name

English

N(SUP 1)-(3-(((1S)-1-PHENYLETHYL)AMINO)PROPYL)BLEOMYCINAMIDE

Common Name

English

N(SUP 1)-(3-(((S)-.ALPHA.-METHYLBENZYL)AMINO)PROPYL)BLEOMYCINAMIDE

Common Name

English

PEPLEOMYCIN

Common Name

English

Peplomycin [WHO-DD]

Common Name

English

peplomycin [INN]

Common Name

English

PEPLOMYCIN [MI]

Common Name

English

PEPLOMYCIN [JAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2311