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

[H][C@@]12C[C@@]3([H])C(C(=O)C4=C(O)C=CC=C4[C@@]3(C)O)=C(O)[C@]1(O)C(=O)C(C(=O)NCN5CCCC5)=C(O)[C@H]2N(C)C

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

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 179 Target ID: CHEMBL2363135 Sources: http://www.drugbank.ca/drugs/DB01301	Binding Agent 1064

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 234 Sources: http://www.ncbi.nlm.nih.gov/pubmed/14066734	Primary		Approved 8429	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 Page: p.229	unhealthy, 19 - 56 n = 45 Health Status: unhealthy Condition: Urethritis Age Group: 19 - 56 Sex: M Population Size: 45 Sources: https://pubmed.ncbi.nlm.nih.gov/5687044 Page: p.229	Sources: https://pubmed.ncbi.nlm.nih.gov/5687044 Page: p.229
350 mg single, intramuscular Studied dose Dose: 350 mg Route: intramuscular Route: single Dose: 350 mg Co-administed with:: Tetracycline phosphate, p.o.(500 mg, single) Sources: https://pubmed.ncbi.nlm.nih.gov/4192321 Page: p.154	unhealthy, 19-41 n = 48 Health Status: unhealthy Condition: Gonorrhoea Age Group: 19-41 Sex: M Population Size: 48 Sources: https://pubmed.ncbi.nlm.nih.gov/4192321 Page: p.154	Sources: https://pubmed.ncbi.nlm.nih.gov/4192321 Page: p.154

Sourcing

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

PubMed

Title	Date	PubMed
Age dependency of rolitetracycline-induced hepatic steatosis.	1981	7344877
Potent inhibitors of human immunodeficiency virus type 1 integrase: identification of a novel four-point pharmacophore and tetracyclines as novel inhibitors.	1997 Dec	9415714
Newer tetracycline derivatives: synthesis, anti-HIV, antimycobacterial activities and inhibition of HIV-1 integrase.	2007 Apr 15	17376679
Combinatorial computational approaches to identify tetracycline derivatives as flavivirus inhibitors.	2007 May 9	17502914

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

Name

Type

Language

ROLITETRACYCLINE

Official 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

SYNTERIN

Brand Name

English

SQ-15659

Code

English

Rolitetracycline [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1595