Monensin A

Monensin A	Last updated: 23/02/2024
(Also known as: monensic acid)

GENERAL INFORMATION

Description

A broad spectrum ionophone veterinary antibotic isolated from Streptomyces cinnamonensis and usually used as the sodium salt of monensin factor A. S. cinnamonensis produces monensin A and monensin B that differ only in the side chain at C-16.

Availability status

Current

Introduction & key dates

1979, first synthesised; mid-1980s, registered for vet use USA

Examples of veterinary uses

Used as a coccidiostat drug as well as a growth promotor

Examples of species treated

Poultry; Cattle; Goats

Approval status

VMR 2013/2033 approval status (GB/UK)

Approved

EU Regulatory approval status

Approved

Chemical structure

Isomerism

Chemical formula

C₃₆H₆₂O₁₁

Canonical SMILES

CCC1(CCC(O1)C2(CCC3(O2)CC(C(C(O3)C(C)C(C(C)C(=O)O)OC)C)O)C)C4C(CC(O4)C5C(CC(C(O5)(CO)O)C)C)C

Isomeric SMILES

CC[C@]1(CC[C@@H](O1)[C@]2(CC[C@@]3(O2)C[C@@H]([C@H]([C@H](O3)[C@H](C)[C@@H]([C@@H](C)C(=O)O)OC)C)O)C)[C@@H]4[C@@H](C[C@H](O4)[C@@H]5[C@H](C[C@H]([C@@](O5)(CO)O)C)C)C

International Chemical Identifier key (InChIKey)

GAOZTHIDHYLHMS-GDMSFIFLSA-N

International Chemical Identifier (InChI)

InChI=1S/C36H62O11/c1-10-34(31-20(3)16-26(43-31)28-19(2)15-21(4)36(41,18-37)46-28)12-11-27(44-34)33(8)13-14-35(47-33)17-25(38)22(5)30(45-35)23(6)29(42-9)24(7)32(39)40/h19-31,37-38,41H,10-18H2,1-9H3,(H,39,40)/t19-,20+,21+,22+,23+,24+,25-,26-,27+,28-,29-,30-,31-,33+,34-,35+,36-/m0/s1

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
Monensin monohydrate	Hydrate

General status

Veterinary substance type

Antibiotic, Antibacterial, Coccidiostat, Feed additive, Growth promotor

Substance groups

Polyether (ionophore)

Minimum active substance purity

Known relevant impurities

Substance origin

Natural

Mode of action

A protein transport inhibitor

Molecular targets

[Intracellular protein transport, Blocker]

CAS RN

17090-79-8

EC number

241-154-0

CIPAC number

US EPA chemical code

PubChem CID

Therapeutic Class

Antiparasitic products, insecticides & repellents: Antiprotozoals

ATCvet Code

QP51AH03

Controlled Drug?

Regulation 37/2010 MRL Classification

Allowed substance (Table 1: Bovine)

Molecular mass

670.87

PIN (Preferred Identification Name)

IUPAC name

4-[2-[5-ethyl-5-[5-[6-hydroxy-6-(hydroxymethyl)-3,5-dimethyl-oxan-2-yl]-3-methyl-oxolan-2-yl]oxolan-2-yl]- 9-hydroxy-2,8-dimethyl-1,6-dioxasp iro[4.5]dec-7-yl]-3-methoxy-2-methyl-pentanoic acid

CAS name

Other status information

Relevant Environmental Water Quality Standards

Physical state

White crystalline solid

Related substances & organisms

monensin sodium

Formulations

Property

Product

Manufacturer

Authorisation Route

Legal Class (GB/UK)

Example products (past and present) using this active

Kexxtone Continuous-Release Intraruminal Device

Elanco GmbH

GB National authorisation

Prescription only medicine to be authorised by a veterinarian (POM-V)

Formulation and application details

Available as continuous-release intraruminal devices

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

4.8

Low

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

Melting point (°C)

104

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

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

5.75 X 10⁰²

Calculated

Log P

2.76

Moderate

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

6.65

Vapour pressure at 20 °C (mPa)

4.27 X 10^-18

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

Monensin is found in turkey excreta and so may be introduced into soil by use of turkey litter as a soil amendment. Monensin is extensively metabolied by cattle

Degradation

Property

Value

Source; quality score; and other information

Interpretation

Soil degradation (days) (aerobic)

DT₅₀ (typical)

7.4

Non-persistent

DT₅₀ (lab at 20 °C)

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

Note

General literature: 1ppm soil conc, only trace remained after 20 days (R4)

Manure DT₅₀ (days)

5.8

Soil & cattle manure

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Stable

Note

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

Value

Stable

Note

Stable at all relevant environmental pH values

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)

K_oc (mL g⁻¹)

Notes and range

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 soil and groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

monensin methyl ester

MME

monensin decyl ester

MDE

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

100

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)

264.2

Eisenia foetida

Moderate

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

Moderate

Soil micro-organisms

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

9.8

Radish
Seedlking emergence, LC₅₀
as mg kg⁻¹

24.1

Mung bean
Seedling emergence, LC₅₀
as mg kg⁻¹; EC₅₀ growth=32.9 mg kg⁻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)

Oncorhynchus mykiss as sodium salt

Moderate

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)

10.7

Daphnia magna as sodium salt

Moderate

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, growth) - Acute 7 day EC₅₀, biomass (mg l⁻¹)

Aquatic plants (rooted, growth) - Acute 14 day EC₅₀, biomass (mg l⁻¹)

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

0.98

Pseudokirchneriella subcapitata Biomass

Moderate

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

0.055

Pseudokirchneriella subcapitata Biomass

Moderate

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)

100

Rat

Moderate

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

Mammals - Inhalation LC₅₀ (mg l⁻¹)

Other Mammal toxicity endpoints

Intraperitoneal LD₅₀ = 15 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 rapidly in the faeces and urine

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 pulmonary edema
May cause gastroinstinal and renal function problems
Possible cardiac, thyroid, kidney and adrenal toxicant

Handling issues

Property

Value and interpretation

General

When heated to decomposition it emits acrid smoke & irritating fumes

CLP classification 2013

WHO Classification

Not listed (Not listed)

UN Number

UN2811

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

monensin A

French

German

Danish

Italian

Spanish

monensina

Greek

Polish

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	23/02/2024
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