Explore a selection of our essential drug information below, or:
Identification
- Summary
Spiramycin is a macrolide antimicrobial agent used in the treatment of various bacterial infections.
- Brand Names
- Rovamycin
- Generic Name
- Spiramycin
- DrugBank Accession Number
- DB06145
- Background
Spiramycin is a primarily bacteriostatic macrolide antimicrobial agent with activity against Gram-positive cocci and rods, Gram-negative cocci and also Legionellae, mycoplasmas, chlamydiae, some types of spirochetes, Toxoplasma gondii and Cryptosporidium. Spiramycin is a 16-membered ring macrolide discovered in 1952 as a product of Streptomyces ambofaciens that has been available in oral formulations since 1955, and parenteral formulations since 1987. Resistant organisms include Enterobacteria, pseudomonads, and moulds.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Spiramycin (DB06145)
- Weight
- Average: 843.065
Monoisotopic: 842.514005071 - Chemical Formula
- C43H74N2O14
- Synonyms
- Demycarosylturimycin H
- Foromacidin A
- Foromacidine A
- Spiramycin 1
- Spiramycin A
- Spiramycin I
Pharmacology
- Indication
Macrolide antibiotic for treatment of various infections.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Bacterial infection •••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
The absolute bioavailability of oral spiramycin is generally within the range of 30 to 40%. After a 1 g oral dose, the maximum serum drug concentration was found to be within the range 0.4 to 1.4 mg/L.
- Mechanism of action
The mechanism of action of macrolides has been a matter of controversy for some time. Spiramycin, a 16-membered macrolide, inhibits translocation by binding to bacterial 50S ribosomal subunits with an apparent 1 : 1 stoichiometry. This antibiotic is a potent inhibitor of the binding to the ribosome of both donor and acceptor substrates. The primary mechanism of action is done by stimulation of dissociation of peptidyl-tRNA from ribosomes during translocation.I
Target Actions Organism A50S ribosomal protein L3 antagonistinhibitorStreptococcus pyogenes serotype M1 - Absorption
The extent of absorption of Spiramycin was shown to be incomplete. Oral bioavailability ranges from 30-39%. Spiramycin has slower rate of absorption than Erythromycin. It has a high pKa (7.9) which could be a result of high degree of ionization in acidic medium of the stomach.
- Volume of distribution
The tissue distribution of spiramycin is extensive. The volume of distribution is in excess of 300 L, and concentrations achieved in bone, muscle, respiratory tract and saliva exceed those found in serum. Spiramycin showed high concentrations in tissues such as: lungs, bronchi, tonsils, and sinuses.
- Protein binding
Low level of protein binding (10-25%).
- Metabolism
Spiramycin is less metabolised than some of the other macrolides. Metabolism has not been well studied. It is mainly done in the liver to the active metabolites.
- Route of elimination
Fecal-biliary route is the primary route of elimination. The secondary route is renal-urinary route.
- Half-life
Intravenous: Young persons (18 to 32 years of age): Approximately 4.5 to 6.2 hours. Elderly persons (73 to 85 years of age): Approximately 9.8 to 13.5 hours.
Oral: 5.5-8 hours, Rectal in children: 8 hours
- Clearance
80% of the administered dose excreted in the bile, which makes the fecal-biliary route is the most important route of elimination. Enterohepatic recycling could also occur. Only 4 to 14% of an administered dose is eliminated through renal-urinary excretion route.
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Cardiac toxicity, specifically QT prolongation (irregular heartbeat; recurrent fainting).
Cholestatic hepatitis (abdominal pain; nausea; vomiting; yellow eyes or skin).
Gastrointestinal toxicity, specifically acute colitis (abdominal pain and tenderness; bloody stools; fever).
Intestinal injury (abdominal pain and tenderness). Ulcerated esophagitis (chest pain; heartburn).- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcenocoumarol The risk or severity of bleeding can be increased when Spiramycin is combined with Acenocoumarol. Ambroxol The risk or severity of methemoglobinemia can be increased when Spiramycin is combined with Ambroxol. Articaine The risk or severity of methemoglobinemia can be increased when Spiramycin is combined with Articaine. Atorvastatin The risk or severity of adverse effects can be increased when Spiramycin is combined with Atorvastatin. BCG vaccine The therapeutic efficacy of BCG vaccine can be decreased when used in combination with Spiramycin. - Food Interactions
- No food interactions are expected.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Rovamycine 250 Capsule 750000 Unit Capsule 750000 unit Oral Odan Laboratories Ltd 1957-12-31 Not applicable Canada 
Rovamycine 500 Capsule 1500000 Unit Capsule 1500000 unit Oral Odan Laboratories Ltd 1957-12-31 Not applicable Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image METİRASİN 1,5 MIU/250 MG FILM TABLET, 10 ADET Spiramycin (1.5 IU) + Metronidazole (250 mg) Tablet, film coated VEM İLAÇ SAN. VE TİC. A.Ş. 2012-01-25 Not applicable Turkey 
METİRASİN 1,5 MIU/250 MG FILM TABLET, 14 ADET Spiramycin (1.5 IU) + Metronidazole (250 mg) Tablet, film coated VEM İLAÇ SAN. VE TİC. A.Ş. 2012-01-25 Not applicable Turkey
Categories
- ATC Codes
- J01RA04 — Spiramycin and metronidazole
- J01RA — Combinations of antibacterials
- J01R — COMBINATIONS OF ANTIBACTERIALS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- Drug Categories
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- Antiparasitic Agents
- Antiprotozoals
- Carbohydrates
- Coccidiostats
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 Enzyme Inhibitors
- Glycosides
- Lactones
- Leucomycins
- Macrolide Antimicrobial
- Macrolides
- Macrolides, Lincosamides and Streptogramins
- Polyketides
- Classification
- Not classified
- Affected organisms
- Bacteria
- Bacteria and protozoa
- Corynebacterium diphtheriae
- Streptococcus pyogenes
- Haemophilus influenzae
- Streptococcus viridans
Chemical Identifiers
- UNII
- 033ECH6IFG
- CAS number
- 24916-50-5
- InChI Key
- ACTOXUHEUCPTEW-CEUOBAOPSA-N
- InChI
- InChI=1S/C43H74N2O14/c1-24-21-29(19-20-46)39(59-42-37(49)36(45(9)10)38(27(4)56-42)58-35-23-43(6,51)41(50)28(5)55-35)40(52-11)31(47)22-33(48)53-25(2)15-13-12-14-16-32(24)57-34-18-17-30(44(7)8)26(3)54-34/h12-14,16,20,24-32,34-42,47,49-51H,15,17-19,21-23H2,1-11H3/b13-12+,16-14+/t24-,25-,26-,27-,28+,29+,30+,31-,32+,34+,35+,36-,37-,38-,39+,40+,41+,42+,43-/m1/s1
- IUPAC Name
- 2-[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-6-{[(2S,3R,4R,5S,6R)-5-{[(2S,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy}-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-10-{[(2R,5S,6R)-5-(dimethylamino)-6-methyloxan-2-yl]oxy}-4-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde
- SMILES
- [H][C@@]1(CC[C@@H]([C@@H](C)O1)N(C)C)O[C@H]1\C=C\C=C\C[C@@H](C)OC(=O)C[C@@H](O)[C@H](OC)[C@@H](O[C@]2([H])O[C@H](C)[C@@H](O[C@@]3([H])C[C@@](C)(O)[C@@H](O)[C@H](C)O3)[C@@H]([C@H]2O)N(C)C)[C@@H](CC=O)C[C@H]1C
References
- General References
- External Links
- PubChem Compound
- 6440717
- PubChem Substance
- 347827756
- ChemSpider
- 4451378
- 9991
- ChEBI
- 85260
- ChEMBL
- CHEMBL453514
- ZINC
- ZINC000257373089
- PDBe Ligand
- SPR
- Wikipedia
- Spiramycin
- PDB Entries
- 1kd1 / 5igz
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Treatment Cryptosporidiosis infection / Human Immunodeficiency Virus (HIV) Infections 1 somestatus stop reason just information to hide 4 Recruiting Treatment Toxoplasmosis 1 somestatus stop reason just information to hide 3 Completed Treatment Toxoplasmosis, Congenital 1 somestatus stop reason just information to hide 1 Completed Treatment Cryptosporidiosis infection / Human Immunodeficiency Virus (HIV) Infections 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, powder, for solution Parenteral 1.5 miu Tablet, film coated Oral 3000.000 iu Tablet, coated Oral 3 million IU Tablet, coated Oral 3 million unit Tablet, film coated Tablet Oral Tablet; tablet, film coated Oral 1.5 IU Tablet, film coated Oral 3 miu Tablet Oral 1500000 UI Tablet Oral 450 mg Tablet, film coated Oral Capsule Oral 750000 unit Capsule Oral 1500000 unit Syrup Oral Tablet, film coated Oral 3000.000 UI Tablet, film coated Oral 1500000 IU Tablet, film coated Oral 1.5 IU Tablet, film coated Oral 3000.000 i.u. Tablet, film coated Oral 1.5 miu Tablet Oral Powder Capsule Oral 500 mg Tablet, film coated Oral 500 mg Syrup Oral 125 mg/5ml - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.196 mg/mL ALOGPS logP 2.99 ALOGPS logP 2.5 Chemaxon logS -3.6 ALOGPS pKa (Strongest Acidic) 12.53 Chemaxon pKa (Strongest Basic) 9.33 Chemaxon Physiological Charge 2 Chemaxon Hydrogen Acceptor Count 15 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 195.38 Å2 Chemaxon Rotatable Bond Count 11 Chemaxon Refractivity 219.25 m3·mol-1 Chemaxon Polarizability 93.01 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Targets
- Kind
- Protein
- Organism
- Streptococcus pyogenes serotype M1
- Pharmacological action
- Yes
- Actions
- AntagonistInhibitor
- General Function
- One of the primary rRNA binding proteins, it binds directly near the 3'-end of the 23S rRNA, where it nucleates assembly of the 50S subunit.
- Specific Function
- rRNA binding
- Gene Name
- rplC
- Uniprot ID
- Q9A1X4
- Uniprot Name
- 50S ribosomal protein L3
- Molecular Weight
- 22438.035 Da
Drug created at November 19, 2007 16:52 / Updated at July 23, 2023 09:46