rolitetracycline   Click here for help

GtoPdb Ligand ID: 12760

Synonyms: pyrrolidinylmethyltetracycline | Reverin® | SQ 15,659 | Syntetrin® | Velacycline®
Approved drug
rolitetracycline is an approved drug (FDA (1959))
Compound class: Synthetic organic
Comment: Rolitetracycline is a parenterally delivered prodrug of tetracycline, an antibacterial that has activity against Gram-negative and Gram-positive bacteria.
Note that the structure shown here matches the CAS-assigned structure and is the same as the ChEBI and ChEMBL entries linked to below. There is no exact match in PubChem for the structure shown here.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 11
Hydrogen bond donors 6
Rotatable bonds 5
Topological polar surface area 170.87
Molecular weight 527.57
XLogP 0.22
No. Lipinski's rules broken 3
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Canonical SMILES C[C@]1(C2=CC=CC(=C2C(=O)C3=C([C@]4([C@@]([H])(C[C@@]31[H])[C@@H](C(=C(C4=O)C(=O)NCN5CCCC5)O)N(C)C)O)O)O)O
Isomeric 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 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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1959))
Withdrawn drug? Yes
Is prodrug? Yes
Active form tetracycline
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
1041 rolitetracycline
Synonyms Click here for help
pyrrolidinylmethyltetracycline | Reverin® | SQ 15,659 | Syntetrin® | Velacycline®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Rolitetracycline
Other databases
BindingDB Ligand 50477463
CAS Registry No. 751-97-3 (source: Scifinder)
ChEMBL Ligand CHEMBL1237046
DrugBank Ligand DB01301
DrugCentral Ligand 2399
GtoPdb PubChem SID 483123308
PubChem CID 54682938
Search Google for chemical match using the InChIKey HMEYVGGHISAPJR-IAHYZSEUSA-N
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UniChem Compound Search for chemical match using the InChIKey HMEYVGGHISAPJR-IAHYZSEUSA-N
UniChem Connectivity Search for chemical match using the InChIKey HMEYVGGHISAPJR-IAHYZSEUSA-N