N-nitrosamide carcinogenic effect

Hello, based on FDA and EMA n-nitroso amide undergo metabolic activation by a different biological pathway than typical nitrosamines, which is α-hydroxylation mechanism that is responsible for the mutagenic and highly potent carcinogenic response observed for many N-nitrosamines. so can we say that n-nitroso amides do not have a carcinogenic effect? or they have but with different mechanism??

the same for nitrosamines where the N -nitroso group is bonded to a nitrogen within an aromatic ring (e.g., nitrosated indole), i think that this must be applied on N-nitroso-Amlodipine which is mentioned in FDA list with category 5, 1500 ng/day limit. can any one explain?

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Hi, @heba-1994
Dr. Ponting explained the mechanism of mutagenicity of n-nitroso ureas and nitrosated indoles in this paper. N-nitroso ureas are direct mutagens, and they are considered to have high potency. This is why read-across and OECD Ames tests may be available for setting AIs of n-nitroso amides.

I think N-nitroso-Amlodipine is not aromatic.

Yosuke

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dear heba-1994,
in addition to Yosuke post, i would like to bring to your attention a separate thrend in this society

in this topic is explained very nice and detailed that N-nitrosoamplodipine is cannot be synthesize
kind regards
Christos

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That can not be said, you have to take them on case by case basis. If you are talking of a true N-nitoso amide of a primary amine, the possiblity of this being carcinogenic is very low to none. But the structure needs to be evaluated. N-nitroso carbamates, guanidines, ureas can be carcinogenic or at least mutagenic.

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Hi Heba, amide itself is not considered as a concern, if that amide further degrades into secondary amine, to be considered at risk.
reference: FDA revision:02 page no 11.

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Here is a blog post from a recent LHASA webinar on nitrosoureas, which was excellent.

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If anybody would like access to @David recent webinar, you need to request access to Lhasa’s marketing team to this address: marketing@lhasalimited.org

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