Spiramycin

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
Thumb
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.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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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

TargetActionsOrganism
A50S ribosomal protein L3
antagonist
inhibitor
Streptococcus 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
Adverseeffects
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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.
DrugInteraction
AcenocoumarolThe risk or severity of bleeding can be increased when Spiramycin is combined with Acenocoumarol.
AtorvastatinThe risk or severity of adverse effects can be increased when Spiramycin is combined with Atorvastatin.
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Spiramycin.
BetamethasoneThe serum concentration of Betamethasone can be increased when it is combined with Spiramycin.
BudesonideThe serum concentration of Budesonide can be increased when it is combined with Spiramycin.
CorticotropinThe serum concentration of Corticotropin can be increased when it is combined with Spiramycin.
Cortisone acetateThe serum concentration of Cortisone acetate can be increased when it is combined with Spiramycin.
DeflazacortThe serum concentration of Deflazacort can be increased when it is combined with Spiramycin.
DexamethasoneThe serum concentration of Dexamethasone can be increased when it is combined with Spiramycin.
DicoumarolThe risk or severity of bleeding can be increased when Spiramycin is combined with Dicoumarol.
Interactions
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Food Interactions
  • No food interactions are expected.

Products

Products2
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Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Rovamycine 250 Capsule 750000 UnitCapsule750000 unitOralOdan Laboratories Ltd1957-12-31Not applicableCanada flag
Rovamycine 500 Capsule 1500000 UnitCapsule1500000 unitOralOdan Laboratories Ltd1957-12-31Not applicableCanada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
METİRASİN 1,5 MIU/250 MG FILM TABLET, 10 ADETSpiramycin (1.5 IU) + Metronidazole (250 mg)Tablet, film coatedVEM İLAÇ SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
METİRASİN 1,5 MIU/250 MG FILM TABLET, 14 ADETSpiramycin (1.5 IU) + Metronidazole (250 mg)Tablet, film coatedVEM İLAÇ SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag

Categories

ATC Codes
J01RA04 — Spiramycin and metronidazoleJ01FA02 — Spiramycin
Drug Categories
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
  1. article [Link]
  2. article [Link]
  3. article [Link]
  4. product info [Link]
PubChem Compound
6440717
PubChem Substance
347827756
ChemSpider
4451378
RxNav
9991
ChEBI
85260
ChEMBL
CHEMBL453514
ZINC
ZINC000257373089
PDBe Ligand
SPR
Wikipedia
Spiramycin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4RecruitingTreatmentToxoplasmosis1
3CompletedTreatmentToxoplasmosis, Congenital1
1CompletedTreatmentCryptosporidiosis infection / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedTreatmentCryptosporidiosis infection / Human Immunodeficiency Virus (HIV) Infections1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, powder, for solutionParenteral
Tablet, coatedOral3 million IU
Tablet, coatedOral3 million unit
Tablet, film coated
TabletOral
Tablet; tablet, film coatedOral
TabletOral1500000 UI
TabletOral450 mg
CapsuleOral750000 unit
CapsuleOral1500000 unit
SyrupOral
Tablet, film coatedOral3000.000 UI
Tablet, film coatedOral
TabletOral
Powder
CapsuleOral500 mg
Tablet, film coatedOral500 mg
SyrupOral125 mg/5ml
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.196 mg/mLALOGPS
logP2.99ALOGPS
logP2.5ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)12.53ChemAxon
pKa (Strongest Basic)9.33ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area195.38 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity219.25 m3·mol-1ChemAxon
Polarizability93.01 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

Drugtargets2
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Kind
Protein
Organism
Streptococcus pyogenes serotype M1
Pharmacological action
Yes
Actions
Antagonist
Inhibitor
General Function
Not Available
Specific Function
Not Available
Gene Name
rplC
Uniprot ID
Q9A1X4
Uniprot Name
50S ribosomal protein L3
Molecular Weight
22438.035 Da

Drug created on November 19, 2007 16:52 / Updated on September 28, 2021 07:54