Rolitetracycline

Pharmaceutical drug

J01AA09 (WHO)

Identifiers

IUPAC name

(2Z,4S,4aS,5aS,6S,12aS)-4-(Dimethylamino)-6,10,11,12a-tetrahydroxy-2-{hydroxy[(pyrrolidin-1-ylmethyl)amino]methylene}-6-methyl-4a,5a,6,12a-tetrahydrotetracene-1,3,12(2H,4H,5H)-trione

CAS Number

751-97-3^Y

PubChem CID

54682938

DrugBank

DB01301^Y

ChemSpider

10469507^Y

UNII

GH9IW85221

KEGG

D02282^Y

ChEMBL

ChEMBL1214184^N

CompTox Dashboard (EPA)

DTXSID7023568

ECHA InfoCard100.010.938

Chemical and physical dataFormulaC₂₇H₃₃N₃O₈Molar mass527.574 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

O=C(NCN1CCCC1)\C2=C(/O)[C@@H](N(C)C)[C@@H]3CC5C(=C(\O)[C@]3(O)C2=O)\C(=O)c4c(O)cccc4[C@@]5(C)O

InChI

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^Y
Key:HMEYVGGHISAPJR-VQCPGFMQSA-N^Y

^NY (what is this?) (verify)

Rolitetracycline is a tetracycline antibiotic.^[1] Tetracycline is N-Mannich base prodrug that is prepared from tetracycline by condensation with pyrrolidine and formaldehyde to produce rolitetracycline. Rolitetracycline is used as an antibacterial drug, a protein synthesis inhibitor, an antiprotozoal drug and a prodrug.^[2]^[3]

References

^ "Rolitetracycline". PubChem. National Library of Medicine. Retrieved 8 June 2020.
^ PubChem. "Rolitetracycline". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-07-29.
^ Smith L (January 1964). "Rolitetracycline, an antibiotic for parenteral use. (syntetrin, velacycline)". JAMA. 187 (2): 141. doi:10.1001/jama.1964.03060150065017. PMID 14066734.

Antibacterials that inhibit protein synthesis (J01A, J01B, J01F, J01G, QJ01XQ)

30S

Aminoglycosides
(initiation inhibitors)

-mycin (Streptomyces)	Streptomycin^# Dihydrostreptomycin Neomycin^# Framycetin Paromomycin^# Ribostamycin Kanamycin Amikacin^# Arbekacin Bekanamycin Dibekacin Tobramycin (+loteprednol) Spectinomycin^# Hygromycin B Totomycin Apramycin Nourseothricin
-micin (Micromonospora)	Gentamicin^# Netilmicin Sisomicin Micronomicin Plazomicin^# Isepamicin Verdamicin Astromicin
other	Butirosin

Tetracycline antibiotics
(tRNA binding)

Tetracyclines	Doxycycline^# Chlortetracycline Clomocycline Demeclocycline Eravacycline Lymecycline Meclocycline^‡ Metacycline Minocycline Omadacycline Oxytetracycline Penimepicycline Rolitetracycline Sarecycline Tetracycline^#
Glycylcyclines	Tigecycline

50S

Oxazolidinone
(initiation inhibitors)

Peptidyl transferase

Amphenicols	Chloramphenicol^# Azidamfenicol Thiamphenicol Florfenicol
Pleuromutilins	Azamulin Lefamulin Retapamulin Tiamulin Valnemulin

MLS (transpeptidation/translocation)

Macrolides	Azithromycin^# Boromycin Carbomycin Carrimycin Clarithromycin^# Dirithromycin Erythromycin^# Flurithromycin Gamithromycin Josamycin Kitasamycin Midecamycin Miocamycin Oleandomycin Rokitamycin Roxithromycin Solithromycin Spiramycin Telithromycin Tildipirosin Tilmicosin Troleandomycin Tulathromycin Tylosin Tylvalosin
Ketolides	Telithromycin^‡ Cethromycin Solithromycin^†
Lincosamides	Clindamycin^# Lincomycin Pirlimycin
Streptogramins	Pristinamycin (IA, IIA, IIB) NXL103 (Flopristin, Linopristin) Quinupristin/dalfopristin (Dalfopristin, Quinupristin) Streptogramin A Streptogramin B Virginiamycin (S1)