ROLITETRACYCLINE

First approved in 1959

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H33N3O8
Molecular Weight	527.5662
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN(C)[C@H]1[C@@H]2C[C@H]3C(C(=O)C4=C(C=CC=C4O)[C@@]3(C)O)=C(O)[C@]2(O)C(=O)C(C(=O)NCN5CCCC5)=C1O

InChI

InChIKey=HMEYVGGHISAPJR-IAHYZSEUSA-N

InChI=1S/C27H33N3O8/c1-26(37)13-7-6-8-16(31)17(13)21(32)18-14(26)11-15-20(29(2)3)22(33)19(24(35)27(15,38)23(18)34)25(36)28-12-30-9-4-5-10-30/h6-8,14-15,20,31,33-34,37-38H,4-5,9-12H2,1-3H3,(H,28,36)/t14-,15-,20-,26+,27-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C27H33N3O8
Molecular Weight	527.5662
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.bioaustralis.com/pdfs/Rolitetracycline.pdf
Curator's Comment: description was created based on several sources, including http://www.innovativesolution.it/rolitetracycline.htm

Rolitetracycline, launched in the late 1950s, was the first of the semi -synthetic tetracyclines. Rolitetracycline is formed by a Mannich condensation of formaldehyde and pyrrolidine with tetracycline. Rolitetracycline is a pro -drug of tetracycline, in which the pyrrolidine moiety improves bioavailability compared with tetracycline. Rolitetracycline has broad spectrum Gram positive activity in vivo, but pH instability limits use to parenteral administration. Rolitetracycline passively diffuses through porin channels in the bacterial membrane and reversibly binds to the 30S ribosomal subunit, preventing binding of tRNA to the mRNA-ribosome complex, and thus interfering with protein synthesis.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial 70S ribosome 180 Target ID: CHEMBL2363135 Sources: http://www.drugbank.ca/drugs/DB01301	Binding Agent 1076

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 235 Sources: http://www.ncbi.nlm.nih.gov/pubmed/14066734	Primary		Approved 8583	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
350 mg 1 times / day multiple, intramuscular Studied dose Dose: 350 mg, 1 times / day Route: intramuscular Route: multiple Dose: 350 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/5687044	unhealthy, 19 - 56 Health Status: unhealthy Age Group: 19 - 56 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/5687044	Sources: https://pubmed.ncbi.nlm.nih.gov/5687044
350 mg single, intramuscular Studied dose Dose: 350 mg Route: intramuscular Route: single Dose: 350 mg Sources: https://pubmed.ncbi.nlm.nih.gov/4192321	unhealthy, 19-41 Health Status: unhealthy Age Group: 19-41 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/4192321	Sources: https://pubmed.ncbi.nlm.nih.gov/4192321

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:63334	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:63334
eMolecules	594054	https://www.emolecules.com/cgi-bin/more?vid=594054
MolPort	MolPort-003-666-732	https://www.molport.com/shop/molecule-link/MolPort-003-666-732
ZINC	ZINC000014880004	http://zinc15.docking.org/substances/ZINC000014880004

PubMed

Title	Date	PubMed
Combinatorial computational approaches to identify tetracycline derivatives as flavivirus inhibitors.	2007-05-09	17502914
Newer tetracycline derivatives: synthesis, anti-HIV, antimycobacterial activities and inhibition of HIV-1 integrase.	2007-04-15	17376679
Potent inhibitors of human immunodeficiency virus type 1 integrase: identification of a novel four-point pharmacophore and tetracyclines as novel inhibitors.	1997-12	9415714
Age dependency of rolitetracycline-induced hepatic steatosis.	1981	7344877

Patents

Sample Use Guides

In Vivo Use Guide

Adult: 350mg intramuscular injection; 275mg i.v. (2-3minutes infusion) once a day. For severe infections the dose can be administered up to three times a day.

Route of Administration: Other

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:02:00 GMT 2025` Edited by `admin` on `Mon Mar 31 18:02:00 GMT 2025`
Record UNII	GH9IW85221
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ROLITETRACYCLINE

Official Name

English

SYNTERIN

Preferred Name

English

ROLITETRACYCLINE [USAN]

Common Name

English

NSC-759177

Code

English

ROLITETRACYCLINE [MI]

Common Name

English

2-NAPHTHACENECARBOXAMIDE, 4-(DIMETHYLAMINO)-1,4,4A,5,5A,6,11,12A-OCTAHYDRO-3,6,10,12,12A-PENTAHYDROXY-6-METHYL-1,11-DIOXO-N-(1-PYRROLIDINYLMETHYL)-, (4S-(4.ALPHA.,4A.ALPHA.,5A.ALPHA.,6.BETA.,12A.ALPHA))

Common Name

English

4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-N-(1-pyrrolidinylmethyl)-2-naphthacenecarboxamide

Common Name

English

ROLITETRACYCLINE [MART.]

Common Name

English

rolitetracycline [INN]

Common Name

English

ROLITETRACYCLINE [JAN]

Common Name

English

SQ 15,659

Code

English

SQ-15659

Code

English

Rolitetracycline [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1595