Rolitetracycline

Rolitetracycline
Systematic (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
Identifiers
CAS Number	751-97-3^Y
ATC code	J01AA09 (WHO)
PubChem	CID 5282179
DrugBank	DB01301^Y
ChemSpider	10469507^Y
UNII	GH9IW85221^Y
KEGG	D02282^Y
ChEMBL	CHEMBL1214184^N
Synonyms	(2Z,4S,4aS,5aS,6S,12aS)-4-dimethylamino-6,10,11,12a-tetrahydroxy-2-[hydroxy-(pyrrolidin-1-ylmethylamino)methylidene]-6-methyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione
Chemical data
Formula	C₂₇H₃₃N₃O₈
Molar mass	527.566 g/mol
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. Tetracycline is N-Mannich base prodrug that is prepared from tetracycline by condensation with pyrrolidine and formaldehyde to produce rolitetracycline.

Antibacterials: protein synthesis inhibitors (J01A, J01B, J01F, J01G, QJ01XQ)

30S

Aminoglycosides
(initiation inhibitors)

-mycin (Streptomyces)	Streptomycin^# Dihydrostreptomycin Neomycin^# Framycetin Paromomycin Ribostamycin Kanamycin^# Amikacin Arbekacin Bekanamycin Dibekacin Tobramycin Spectinomycin^# Hygromycin B Paromomycin

-micin (Micromonospora)	Gentamicin^# Netilmicin Sisomicin Isepamicin Verdamicin Astromicin

Tetracycline antibiotics
(tRNA binding)

Tetracyclines	Doxycycline^# Chlortetracycline Clomocycline Demeclocycline Lymecycline Meclocycline Metacycline Minocycline Oxytetracycline Penimepicycline Rolitetracycline Tetracycline

Glycylcyclines	Tigecycline

50S

Oxazolidinone
(initiation inhibitors)

Peptidyl transferase

Amphenicols	Chloramphenicol^# Azidamfenicol Thiamphenicol Florfenicol

Pleuromutilins	Retapamulin Tiamulin Valnemulin

MLS (transpeptidation/translocation)

Macrolides	Azithromycin^# Clarithromycin Dirithromycin Erythromycin^# Flurithromycin Josamycin Midecamycin Miocamycin Oleandomycin Rokitamycin Roxithromycin Spiramycin Troleandomycin Tylosin Ketolides Telithromycin Cethromycin Solithromycin^†

Lincosamides	Clindamycin^# Lincomycin Pirlimycin

Streptogramins	Pristinamycin Quinupristin/dalfopristin Virginiamycin

EF-G

Steroid antibacterials	Fusidic acid

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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