Clindamycin

Clindamycin	Last updated: 07/09/2025
(Also known as: 7(S)-chloro-7-deoxylincomycin; chlolincocin; chlorlincocin; U-21251)

GENERAL INFORMATION

Description

A lincosamide veterinary antibiotic used to treat a range of bacterial infections

Examples of veterinary uses

Used primarily to treat infections caused by susceptible anaerobic bacteria and is effective against bacteria that infect the skin, oral cavity, bone and respiratory tract

Examples of species treated

Dogs; Cats

Approval status

VMR 2013/2033 approval status (GB/UK)

Approved - usually supplied as a prescription only medicine to be authorised by a veterinarian (POM-V)

EU Regulatory approval status

Approved

Chemical structure

Isomerism

Clindamycin exhibits stereoisomerism, specifically diastereomerism, due to its multiple chiral centres within the lincosamide framework. It is a semi-synthetic derivative of lincomycin, and its biological activity is highly dependent on its precise three-dimensional configuration. The molecule contains several asymmetric carbon atoms, including those in the amino acid and sugar-like portions of the structure, which influence its ability to bind effectively to the bacterial 50S ribosomal subunit. Among its stereoisomers, only the active isomer, typically the 7(S)-chloro-7-deoxylincomycin configuration, is used therapeutically, as other isomers may lack antibacterial potency or exhibit different pharmacokinetics.

Chemical formula

C₁₈H₃₃ClN₂O₅S

Canonical SMILES

CCCC1CC(N(C1)C)C(=O)NC(C2C(C(C(C(O2)SC)O)O)O)C(C)Cl

Isomeric SMILES

CCC[C@@H]1C[C@H](N(C1)C)C(=O)NC([C@@H]2[C@@H]([C@@H]([C@H]([C@H](O2)SC)O)O)O)[C@H](C)Cl

International Chemical Identifier key (InChIKey)

KDLRVYVGXIQJDK-GOBYPPTJSA-N

International Chemical Identifier (InChI)

InChI=1S/C18H33ClN2O5S/c1-5-6-10-7-11(21(3)8-10)17(25)20-12(9(2)19)16-14(23)13(22)15(24)18(26-16)27-4/h9-16,18,22-24H,5-8H2,1-4H3,(H,20,25)/t9-,10+,11-,12+,13-,14+,15+,16+,18+/m0/s1

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
Clindamycin hydrochloride monohydrate	Variant

General status

Veterinary substance type

Antibiotic, Antibacterial, Medicinal drug

Substance groups

Lincosamide

Minimum active substance purity

Known relevant impurities

Substance origin

Semi-synthetic

Mode of action

A bacterial protein synthesis inhibitor that works by inhibiting ribosomal translocation

Molecular targets

[50S ribosomal protein L10, Antagonist], [23S rRNA, Antagonist]

CAS RN

18323-44-9

EC number

242-209-1

CIPAC number

US EPA chemical code

PubChem CID

446598

Therapeutic Class

Antiinfectants for systemic use: Antibacterials for systemic use

ATCvet Code

QJ01FF01

Controlled Drug?

Regulation 37/2010 MRL Classification

Molecular mass

424.98

PIN (Preferred Identification Name)

IUPAC name

(2S,4R)-N-{2-chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl}-1-methyl-4-propylpyrrolidine-2-carboxamide

CAS name

methyl-7-chloro-6,7,8-trideoxy-6-[[[(2S,4R)-1-methyl-4-propyl-2-pyrrolidinyl]carbonyl]amino]-1-thio--threo-a-D-galacto-octopyranoside

Forever chemical

Other status information

Relevant Environmental Water Quality Standards

Physical state

Yellow, amorphous solid as parent, white liquid as phosphate

Related substances & organisms

lincomycin

pirlimycin hydrochloride

Commercial

Property

Value

Availability status

Current

Introduction & key dates

1966, first synthesised

Example manufacturers & suppliers of products using this active now or historically

Zoetis UK Ltd
Chanelle Animal Health Ltd
Norbrook Laboratories Ltd
Ceva Animal Health Ltd

Example products using this active

Antirobe Capsules
Clinacin Tablets
Mycinor Tablets

Formulation and application details

Usually supplied in tablet or capsule form for oral administration

Commercial production

Clindamycin is produced through a semi-synthetic process starting from lincomycin, a naturally occurring antibiotic derived from Streptomyces lincolnensis. The key transformation involves replacing the 7-hydroxyl group of lincomycin with a chlorine atom via a Vilsmeier–Haack reaction, typically using reagents like phosphorus oxychloride and dimethylformamide in a halogenated solvent such as dichloroethane. This step enhances lipophilicity and improves tissue penetration. The resulting clindamycin free base is then converted into its hydrochloride salt by reacting with hydrochloric acid in ethanol, forming clindamycin hydrochloride alcoholate, which is purified through centrifugation and dealcoholisation under controlled conditions

Impact on climate of production and use

Published GHG data is not available for most pharmaceuticals. However, according to industry, global averages suggest producing 1 kg of a typical active pharmaceutical ingredient can range from 10 to 100 kg CO₂e for small molecule drugs and potentially up to 1000 kg CO₂e for complex biologicals such as vaccines, depending on the drug type, its formulation, complexity of synthesis, solvent recovery, and energy sources used.

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

Solubility - In water at 20 °C (mg l⁻¹)

30.6

Moderate

Solubility - In organic solvents at 20 °C (mg l⁻¹)

Melting point (°C)

141

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

Flashpoint (°C)

334

Octanol-water partition coefficient at pH 7, 20 °C

1.45 X 10⁰²

Calculated

Log P

2.16

Low

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.29

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

7.02 X 10^-12

Low volatility

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

Surface tension (mN m⁻¹)

Refractive Index

Environmental release

Degradation

Property

Value

Source; quality score; and other information

Interpretation

Soil degradation (days) (aerobic)

DT₅₀ (typical)

DT₅₀ (lab at 20 °C)

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

Note

Manure DT₅₀ (days)

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Note

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

Stable

Note

Hydrolysis not expected under environmental conditions

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

Sediment phase only DT₅₀ (days)

Air degradation

As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.

Decay in stored produce DT₅₀

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

Moderately mobile

K_oc (mL g⁻¹)

360

Notes and range

Estimated

Freundlich

K_f (mL g⁻¹)

K_foc (mL g⁻¹)

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

Bio-concentration factor

BCF (l kg⁻¹)

CT₅₀ (days)

Known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

1832

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

Birds - Acute LD₅₀ (mg kg⁻¹)

Birds - Short term dietary (LC₅₀/LD₅₀)

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)

Soil micro-organisms

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

Vegetative vigour ER₅₀ (g ha⁻¹)

Seedling emergence ER₅₀ (g ha⁻¹)

Honeybees (Apis spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Chronic

Notes

Bumblebees (Bombus spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Mason bees (Osmia spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Other bee species (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Other bee species (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Beneficial insects (Ladybirds)

Beneficial insects (Lacewings)

Beneficial insects (Parasitic wasps)

Beneficial insects (Predatory mites)

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)

Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

Aquatic Plants (free-floating, fonds growth, fresh) - 7 day (mg l⁻¹)

Aquatic plants (rooted, growth rate, fresh) - 14 day (mg l⁻¹)

Algae - Acute (growth rate, fresh; mg l⁻¹)

Algae - Chronic (growth rate, fresh; mg l⁻¹)

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves

HUMAN HEALTH AND PROTECTION

General

Property

Value

Source; quality score; and other information

Interpretation

Threshold of Toxicological Concern (Cramer Class)

High (class III)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

1832

Rat

Moderate

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

Mammals - Inhalation LC₅₀ (mg l⁻¹)

Other Mammal toxicity endpoints

Subcutaneous LD₅₀ = 2618 mg kg⁻¹

Rat

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

Exposure Routes

Public

Occupational

Mammalian dose elimination route and rate

Excreted mainly in bile with around 20% eliminated in the faeces and urine. Secreted in breast milk.

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

May cause severe intestinal problems including diarrhoea, nausea & colitis

Handling issues

Property

Value and interpretation

General

In a fire may decompose and produce irritating vapors and toxic compounds

CLP classification 2013

WHO Classification

Not listed (Not listed)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

clindamycin

French

clindamycine

German

Danish

Italian

Spanish

clindamicina

Greek

Polish

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	07/09/2025
Contact:	aeru@herts.ac.uk
Please cite as:	Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242